# Electronic Supplementary Material (ESI) for ChemComm.
# 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_CMPYA
_database_code_depnum_ccdc_archive 'CCDC 1062094'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 4-chloro-3-methoxy-1H-pyrrole-2-aldehyde 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 Cl N O2'
_chemical_formula_sum            'C6 H6 Cl N O2'
_chemical_formula_weight         159.57

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   12.132(3)
_cell_length_b                   6.7332(17)
_cell_length_c                   8.752(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.331(4)
_cell_angle_gamma                90.00
_cell_volume                     714.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4303
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.08

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
;
Sheldrick,G.M.,(2003),University of gottingen,Germany
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7026
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         26.13
_reflns_number_total             1422
_reflns_number_gt                1359
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0536P)²+0.3266P] 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         1422
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.233
_refine_ls_restrained_S_all      1.233
_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
Cl1 Cl 0.36873(5) 1.19021(12) 0.73138(7) 0.0631(3) Uani 1 1 d . . .
O2 O 0.02089(14) 0.9188(3) 0.2385(2) 0.0586(5) Uani 1 1 d . . .
N1 N 0.12608(16) 1.1943(3) 0.4383(2) 0.0437(5) Uani 1 1 d . . .
C3 C 0.23457(18) 0.9600(3) 0.5381(2) 0.0434(5) Uani 1 1 d . . .
O1 O 0.27765(15) 0.7777(3) 0.5714(2) 0.0582(5) Uani 1 1 d . . .
C4 C 0.14844(18) 0.9950(3) 0.4340(3) 0.0428(5) Uani 1 1 d . . .
C1 C 0.19468(19) 1.2845(3) 0.5373(3) 0.0454(5) Uani 1 1 d . . .
H1 H 0.1958 1.4196 0.5595 0.054 Uiso 1 1 calc R . .
C5 C 0.0910(2) 0.8630(4) 0.3324(3) 0.0488(6) Uani 1 1 d . . .
H5 H 0.1074 0.7283 0.3376 0.059 Uiso 1 1 calc R . .
C2 C 0.26362(18) 1.1429(4) 0.6010(2) 0.0431(5) Uani 1 1 d . . .
C6 C 0.3839(3) 0.7442(5) 0.5112(5) 0.0795(9) Uani 1 1 d . . .
H6A H 0.3792 0.7467 0.4016 0.119 Uiso 1 1 calc R . .
H6B H 0.4109 0.6170 0.5447 0.119 Uiso 1 1 calc R . .
H6C H 0.4335 0.8462 0.5467 0.119 Uiso 1 1 calc R . .
H1N H 0.081(2) 1.250(4) 0.383(3) 0.048(7) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0554(4) 0.0805(5) 0.0526(4) -0.0083(3) -0.0152(3) -0.0031(3)
O2 0.0582(10) 0.0519(10) 0.0648(11) 0.0010(8) -0.0177(8) -0.0106(8)
N1 0.0421(10) 0.0421(10) 0.0466(11) 0.0038(8) -0.0069(8) 0.0031(8)
C3 0.0419(11) 0.0442(12) 0.0442(12) 0.0050(9) 0.0010(9) -0.0015(9)
O1 0.0543(10) 0.0464(10) 0.0736(12) 0.0140(8) -0.0030(9) 0.0075(8)
C4 0.0404(11) 0.0416(12) 0.0462(12) 0.0030(9) -0.0006(9) -0.0026(9)
C1 0.0477(12) 0.0414(12) 0.0469(12) -0.0039(9) -0.0002(10) -0.0015(10)
C5 0.0478(13) 0.0426(12) 0.0556(14) 0.0022(10) -0.0037(10) -0.0061(10)
C2 0.0388(11) 0.0518(13) 0.0387(11) -0.0006(9) -0.0008(9) -0.0037(9)
C6 0.0606(18) 0.0665(19) 0.111(3) -0.0081(18) 0.0001(17) 0.0196(15)

_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 C2 1.721(2) . ?
O2 C5 1.228(3) . ?
N1 C1 1.334(3) . ?
N1 C4 1.370(3) . ?
C3 O1 1.363(3) . ?
C3 C4 1.390(3) . ?
C3 C2 1.391(3) . ?
O1 C6 1.422(3) . ?
C4 C5 1.428(3) . ?
C1 C2 1.378(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 110.0(2) . . ?
O1 C3 C4 124.8(2) . . ?
O1 C3 C2 128.3(2) . . ?
C4 C3 C2 106.8(2) . . ?
C3 O1 C6 114.2(2) . . ?
N1 C4 C3 107.1(2) . . ?
N1 C4 C5 122.2(2) . . ?
C3 C4 C5 130.7(2) . . ?
N1 C1 C2 108.1(2) . . ?
O2 C5 C4 123.2(2) . . ?
C1 C2 C3 107.87(19) . . ?
C1 C2 Cl1 124.99(19) . . ?
C3 C2 Cl1 127.11(18) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.13
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_CMCPYA
_database_code_depnum_ccdc_archive 'CCDC 1062095'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 3-chloro-5-formyl-4-methoxy-1H-pyrrole-2-nitrile 
;
_chemical_name_common            pyrrole
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 Cl N2 O2'
_chemical_formula_sum            'C7 H5 Cl N2 O2'
_chemical_formula_weight         184.58

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

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

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

_cell_length_a                   6.037(2)
_cell_length_b                   8.101(3)
_cell_length_c                   9.222(3)
_cell_angle_alpha                70.622(5)
_cell_angle_beta                 74.480(5)
_cell_angle_gamma                85.612(5)
_cell_volume                     409.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2536
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             188
_exptl_absorpt_coefficient_mu    0.422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
;
Sheldrick,G.M.,(2003),University of gottingen,Germany
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4234
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         26.21
_reflns_number_total             1612
_reflns_number_gt                1553
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0369P)²+0.5260P] 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         1612
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.1610
_refine_ls_wR_factor_gt          0.1596
_refine_ls_goodness_of_fit_ref   1.367
_refine_ls_restrained_S_all      1.367
_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
Cl1 Cl 0.18430(18) 0.92439(15) -0.15160(13) 0.0577(4) Uani 1 1 d . . .
O1 O 0.2638(5) 0.8367(4) 0.1842(3) 0.0557(8) Uani 1 1 d . . .
N1 N 0.7117(5) 0.6525(4) -0.0517(4) 0.0407(7) Uani 1 1 d . . .
O2 O 0.9138(5) 0.5201(4) 0.1970(3) 0.0616(8) Uani 1 1 d . . .
C3 C 0.4196(6) 0.7759(5) 0.0805(4) 0.0398(8) Uani 1 1 d . . .
C1 C 0.5806(6) 0.7321(5) -0.1526(4) 0.0379(8) Uani 1 1 d . . .
C4 C 0.6205(6) 0.6779(5) 0.0923(4) 0.0395(8) Uani 1 1 d . . .
N2 N 0.6695(7) 0.7275(6) -0.4381(4) 0.0731(12) Uani 1 1 d . . .
C6 C 0.6333(7) 0.7296(5) -0.3119(5) 0.0476(9) Uani 1 1 d . . .
C2 C 0.3983(6) 0.8093(5) -0.0738(4) 0.0392(8) Uani 1 1 d . . .
C5 C 0.7413(7) 0.6071(5) 0.2146(5) 0.0478(9) Uani 1 1 d . . .
H5 H 0.6852 0.6289 0.3107 0.057 Uiso 1 1 calc R . .
C7 C 0.2621(8) 0.7735(7) 0.3469(5) 0.0678(13) Uani 1 1 d . . .
H7A H 0.2605 0.6479 0.3829 0.102 Uiso 1 1 calc R . .
H7B H 0.1276 0.8145 0.4076 0.102 Uiso 1 1 calc R . .
H7C H 0.3971 0.8152 0.3608 0.102 Uiso 1 1 calc R . .
H1N H 0.826(7) 0.598(5) -0.074(5) 0.048(12) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0498(6) 0.0647(7) 0.0643(7) -0.0226(5) -0.0270(5) 0.0188(5)
O1 0.0529(16) 0.0682(19) 0.0502(16) -0.0315(14) -0.0107(13) 0.0237(14)
N1 0.0346(16) 0.0501(19) 0.0409(17) -0.0232(14) -0.0076(13) 0.0103(14)
O2 0.0568(17) 0.080(2) 0.0578(18) -0.0346(16) -0.0230(14) 0.0314(16)
C3 0.0369(18) 0.0400(19) 0.045(2) -0.0191(16) -0.0088(15) 0.0045(15)
C1 0.0358(18) 0.0419(19) 0.0366(18) -0.0133(15) -0.0100(14) 0.0015(15)
C4 0.0379(18) 0.044(2) 0.0401(19) -0.0194(16) -0.0095(15) 0.0042(15)
N2 0.074(3) 0.106(3) 0.046(2) -0.033(2) -0.0185(19) 0.015(2)
C6 0.043(2) 0.056(2) 0.045(2) -0.0188(18) -0.0120(17) 0.0053(17)
C2 0.0356(18) 0.041(2) 0.044(2) -0.0172(16) -0.0116(15) 0.0063(15)
C5 0.048(2) 0.057(2) 0.045(2) -0.0262(18) -0.0153(17) 0.0154(19)
C7 0.063(3) 0.094(4) 0.046(2) -0.034(2) -0.006(2) 0.026(3)

_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 C2 1.709(4) . ?
O1 C3 1.342(4) . ?
O1 C7 1.413(5) . ?
N1 C1 1.352(4) . ?
N1 C4 1.372(5) . ?
O2 C5 1.217(4) . ?
C3 C2 1.397(5) . ?
C3 C4 1.407(5) . ?
C1 C2 1.378(5) . ?
C1 C6 1.424(5) . ?
C4 C5 1.442(5) . ?
N2 C6 1.131(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C7 119.4(3) . . ?
C1 N1 C4 109.9(3) . . ?
O1 C3 C2 120.5(3) . . ?
O1 C3 C4 132.5(3) . . ?
C2 C3 C4 107.0(3) . . ?
N1 C1 C2 108.4(3) . . ?
N1 C1 C6 122.8(3) . . ?
C2 C1 C6 128.8(3) . . ?
N1 C4 C3 106.9(3) . . ?
N1 C4 C5 118.1(3) . . ?
C3 C4 C5 135.0(3) . . ?
N2 C6 C1 178.3(4) . . ?
C1 C2 C3 107.8(3) . . ?
C1 C2 Cl1 125.8(3) . . ?
C3 C2 Cl1 126.4(3) . . ?
O2 C5 C4 122.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        26.21
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_CMBPYDA
_database_code_depnum_ccdc_archive 'CCDC 1062096'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 4,4'-dichloro-3,3'-dimethoxy-1H,1'H-[2,2'-bipyrrole]-5,5'-dialdehyde 
;
_chemical_name_common            bipyrrole
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 Cl2 N2 O4'
_chemical_formula_sum            'C12 H10 Cl2 N2 O4'
_chemical_formula_weight         317.12

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   4.4859(8)
_cell_length_b                   20.457(4)
_cell_length_c                   14.700(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.600(3)
_cell_angle_gamma                90.00
_cell_volume                     1337.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2111
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9201
_exptl_absorpt_correction_T_max  0.9383
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 Sheldrick,G.M.,(2003),University of gottingen,Germany 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13757
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         26.04
_reflns_number_total             2644
_reflns_number_gt                2587
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0425P)²+6.1420P] 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         2644
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_gt           0.1507
_refine_ls_wR_factor_ref         0.2669
_refine_ls_wR_factor_gt          0.2654
_refine_ls_goodness_of_fit_ref   1.507
_refine_ls_restrained_S_all      1.507
_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
Cl2 Cl 0.1610(6) 0.75993(10) 0.86608(16) 0.0621(7) Uani 1 1 d . . .
Cl1 Cl 0.8309(6) 1.11122(12) 0.60554(15) 0.0635(7) Uani 1 1 d . . .
N2 N 0.1536(13) 0.9483(3) 0.8815(4) 0.0343(14) Uani 1 1 d . . .
N1 N 0.5186(15) 1.0552(3) 0.8253(4) 0.0408(16) Uani 1 1 d . . .
O1 O 0.5155(11) 0.9679(3) 0.6190(3) 0.0447(14) Uani 1 1 d . . .
C9 C -0.1277(16) 0.8819(4) 0.9782(5) 0.0379(17) Uani 1 1 d . . .
H9 H -0.1922 0.8404 0.9925 0.045 Uiso 1 1 calc R . .
O4 O -0.2097(13) 0.9291(3) 1.0200(4) 0.0501(14) Uani 1 1 d . . .
O3 O 0.6702(17) 1.1852(3) 0.8853(4) 0.0690(19) Uani 1 1 d . . .
C4 C 0.4632(16) 0.9992(3) 0.7761(5) 0.0351(16) Uani 1 1 d . . .
C6 C 0.3494(16) 0.8757(4) 0.7952(5) 0.0388(17) Uani 1 1 d . . .
C5 C 0.3280(15) 0.9425(4) 0.8129(5) 0.0351(16) Uani 1 1 d . . .
O2 O 0.5242(12) 0.8485(3) 0.7361(4) 0.0484(14) Uani 1 1 d . . .
C3 C 0.5598(14) 1.0099(4) 0.6911(5) 0.0346(16) Uani 1 1 d . . .
C1 C 0.6504(18) 1.1016(4) 0.7763(5) 0.0438(18) Uani 1 1 d . . .
C7 C 0.1896(17) 0.8431(3) 0.8552(5) 0.0385(18) Uani 1 1 d . . .
C11 C 0.7811(19) 0.9453(5) 0.5862(7) 0.063(3) Uani 1 1 d . . .
H11A H 0.9056 0.9819 0.5755 0.094 Uiso 1 1 calc R . .
H11B H 0.7280 0.9217 0.5299 0.094 Uiso 1 1 calc R . .
H11C H 0.8889 0.9169 0.6310 0.094 Uiso 1 1 calc R . .
C8 C 0.0631(15) 0.8885(3) 0.9086(5) 0.0340(16) Uani 1 1 d . . .
C12 C 0.364(2) 0.8167(4) 0.6578(6) 0.059(2) Uani 1 1 d . . .
H12A H 0.2000 0.7920 0.6763 0.088 Uiso 1 1 calc R . .
H12B H 0.4974 0.7877 0.6313 0.088 Uiso 1 1 calc R . .
H12C H 0.2872 0.8488 0.6132 0.088 Uiso 1 1 calc R . .
C2 C 0.6829(15) 1.0720(4) 0.6937(5) 0.0397(18) Uani 1 1 d . . .
C10 C 0.726(2) 1.1644(4) 0.8126(6) 0.054(2) Uani 1 1 d . . .
H10 H 0.8288 1.1922 0.7773 0.065 Uiso 1 1 calc R . .
H2N H 0.126(13) 0.980(3) 0.919(4) 0.016(16) Uiso 1 1 d . . .
H1N H 0.450(14) 1.065(3) 0.871(5) 0.019(17) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl2 0.0893(18) 0.0317(10) 0.0659(15) -0.0028(10) 0.0124(13) -0.0014(11)
Cl1 0.0743(16) 0.0716(16) 0.0495(13) 0.0060(11) 0.0269(11) -0.0174(13)
N2 0.036(3) 0.038(3) 0.030(3) -0.010(3) 0.010(3) -0.001(3)
N1 0.047(4) 0.046(4) 0.030(3) -0.003(3) 0.009(3) 0.005(3)
O1 0.033(3) 0.064(4) 0.036(3) -0.012(3) 0.005(2) -0.002(3)
C9 0.042(4) 0.032(4) 0.040(4) 0.000(3) 0.006(3) -0.007(3)
O4 0.056(4) 0.048(3) 0.050(3) -0.008(3) 0.021(3) -0.010(3)
O3 0.103(6) 0.052(4) 0.053(4) -0.006(3) 0.013(4) -0.007(4)
C4 0.033(4) 0.035(4) 0.037(4) -0.006(3) 0.004(3) 0.002(3)
C6 0.031(4) 0.039(4) 0.044(4) -0.002(3) -0.003(3) 0.009(3)
C5 0.028(4) 0.044(4) 0.032(4) 0.000(3) 0.001(3) 0.006(3)
O2 0.049(3) 0.050(3) 0.048(3) -0.009(3) 0.012(3) 0.016(3)
C3 0.016(3) 0.056(5) 0.031(4) 0.000(3) 0.002(3) -0.002(3)
C1 0.046(5) 0.042(4) 0.045(4) 0.002(4) 0.011(4) -0.003(4)
C7 0.048(5) 0.027(4) 0.037(4) -0.001(3) -0.005(3) 0.003(3)
C11 0.042(5) 0.076(6) 0.072(6) -0.013(5) 0.017(5) 0.008(5)
C8 0.030(4) 0.031(4) 0.038(4) -0.001(3) -0.007(3) -0.005(3)
C12 0.070(6) 0.049(5) 0.057(6) -0.013(4) 0.009(5) 0.010(5)
C2 0.021(3) 0.063(5) 0.035(4) 0.000(4) 0.007(3) -0.003(3)
C10 0.057(6) 0.052(5) 0.052(5) 0.009(4) 0.004(4) -0.005(4)

_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
Cl2 C7 1.715(7) . ?
Cl1 C2 1.730(7) . ?
N2 C5 1.361(9) . ?
N2 C8 1.364(9) . ?
N1 C4 1.361(9) . ?
N1 C1 1.373(10) . ?
O1 C3 1.357(8) . ?
O1 C11 1.421(9) . ?
C9 O4 1.226(9) . ?
C9 C8 1.425(10) . ?
O3 C10 1.208(10) . ?
C4 C3 1.393(10) . ?
C4 C5 1.446(10) . ?
C6 O2 1.363(9) . ?
C6 C7 1.380(11) . ?
C6 C5 1.398(10) . ?
O2 C12 1.431(10) . ?
C3 C2 1.384(11) . ?
C1 C2 1.381(10) . ?
C1 C10 1.415(11) . ?
C7 C8 1.385(10) . ?

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
C5 N2 C8 111.1(6) . . ?
C4 N1 C1 111.4(6) . . ?
C3 O1 C11 115.4(6) . . ?
O4 C9 C8 122.3(7) . . ?
N1 C4 C3 106.7(6) . . ?
N1 C4 C5 122.2(6) . . ?
C3 C4 C5 131.1(7) . . ?
O2 C6 C7 127.0(7) . . ?
O2 C6 C5 125.3(7) . . ?
C7 C6 C5 107.4(7) . . ?
N2 C5 C6 106.5(6) . . ?
N2 C5 C4 121.2(6) . . ?
C6 C5 C4 132.2(7) . . ?
C6 O2 C12 115.3(6) . . ?
O1 C3 C2 128.2(6) . . ?
O1 C3 C4 124.7(7) . . ?
C2 C3 C4 106.9(6) . . ?
N1 C1 C2 105.1(7) . . ?
N1 C1 C10 122.0(7) . . ?
C2 C1 C10 133.0(8) . . ?
C6 C7 C8 109.0(6) . . ?
C6 C7 Cl2 126.2(6) . . ?
C8 C7 Cl2 124.9(6) . . ?
N2 C8 C7 106.0(6) . . ?
N2 C8 C9 121.6(6) . . ?
C7 C8 C9 132.3(7) . . ?
C1 C2 C3 109.8(7) . . ?
C1 C2 Cl1 123.4(6) . . ?
C3 C2 Cl1 126.6(6) . . ?
O3 C10 C1 125.8(8) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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_TCTMPo
_database_code_depnum_ccdc_archive 'CCDC 1062097'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2,7,12,17-tetrachloro-3,6,13,16-tetramethoxy-porphycene 
;
_chemical_name_common            porphycene
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Cl4 N4 O4'
_chemical_formula_sum            'C24 H18 Cl4 N4 O4'
_chemical_formula_weight         568.22

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   3.9469(2)
_cell_length_b                   27.0301(15)
_cell_length_c                   10.9065(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.544(5)
_cell_angle_gamma                90.00
_cell_volume                     1150.65(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1472
_cell_measurement_theta_min      4.4670
_cell_measurement_theta_max      71.7320

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    5.047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.492
_exptl_absorpt_correction_T_max  0.603
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3733
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.41
_diffrn_reflns_theta_max         66.58
_reflns_number_total             1961
_reflns_number_gt                1455
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material  
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;

_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)+(0.1953P)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         1961
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.2799
_refine_ls_wR_factor_gt          0.2148
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_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
Cl2 Cl 1.3877(4) 0.58562(5) 0.42327(11) 0.0695(6) Uani 1 1 d . . .
Cl1 Cl 0.2619(4) 0.67989(5) -0.29717(13) 0.0787(6) Uani 1 1 d . . .
N1 N 0.4290(10) 0.56204(14) -0.0893(3) 0.0494(9) Uani 1 1 d . . .
N2 N 0.8097(11) 0.53150(14) 0.1329(3) 0.0516(9) Uani 1 1 d . . .
O2 O 1.0865(12) 0.65612(14) 0.1966(3) 0.0738(11) Uani 1 1 d . . .
C1 C 0.2710(13) 0.58570(17) -0.1935(4) 0.0516(11) Uani 1 1 d . . .
C3 C 0.5884(13) 0.64271(17) -0.0755(4) 0.0556(11) Uani 1 1 d . . .
C7 C 1.1292(13) 0.5735(2) 0.2844(4) 0.0560(11) Uani 1 1 d . . .
C4 C 0.6218(12) 0.59536(16) -0.0157(4) 0.0483(10) Uani 1 1 d . . .
O1 O 0.7615(11) 0.68423(13) -0.0330(4) 0.0711(11) Uani 1 1 d . . .
C9 C 1.0604(13) 0.48257(19) 0.3161(4) 0.0562(11) Uani 1 1 d . . .
H9 H 1.2026 0.4867 0.3914 0.067 Uiso 1 1 calc R . .
C8 C 0.9984(13) 0.52578(18) 0.2465(4) 0.0526(11) Uani 1 1 d . . .
C5 C 0.8072(12) 0.57987(16) 0.0993(4) 0.0481(10) Uani 1 1 d . . .
C2 C 0.3810(13) 0.63631(17) -0.1832(4) 0.0553(11) Uani 1 1 d . . .
C6 C 1.0143(13) 0.60706(18) 0.1960(4) 0.0539(11) Uani 1 1 d . . .
C10 C 0.0524(13) 0.56503(18) -0.2925(4) 0.0559(12) Uani 1 1 d . . .
H10 H -0.0324 0.5876 -0.3538 0.067 Uiso 1 1 calc R . .
C12 C 0.944(2) 0.6843(2) 0.2871(7) 0.087(2) Uani 1 1 d . . .
H12A H 0.6990 0.6807 0.2738 0.130 Uiso 1 1 calc R . .
H12B H 1.0024 0.7185 0.2799 0.130 Uiso 1 1 calc R . .
H12C H 1.0338 0.6726 0.3685 0.130 Uiso 1 1 calc R . .
C11 C 0.558(2) 0.7253(2) -0.0084(8) 0.0879(19) Uani 1 1 d . . .
H11A H 0.4148 0.7351 -0.0833 0.132 Uiso 1 1 calc R . .
H11B H 0.7047 0.7524 0.0221 0.132 Uiso 1 1 calc R . .
H11C H 0.4178 0.7163 0.0528 0.132 Uiso 1 1 calc R . .
H1N H 0.35(3) 0.523(3) -0.085(10) 0.16(4) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl2 0.0720(10) 0.0809(10) 0.0525(8) -0.0053(5) -0.0010(6) -0.0100(6)
Cl1 0.0989(13) 0.0592(8) 0.0744(9) 0.0201(6) 0.0010(8) 0.0095(7)
N1 0.054(2) 0.050(2) 0.0443(17) 0.0009(14) 0.0076(15) 0.0053(17)
N2 0.063(2) 0.0480(19) 0.0446(17) -0.0005(14) 0.0107(16) -0.0001(17)
O2 0.100(3) 0.057(2) 0.065(2) -0.0035(16) 0.0127(19) -0.023(2)
C1 0.056(3) 0.051(2) 0.050(2) 0.0022(16) 0.0143(19) 0.0086(19)
C3 0.060(3) 0.046(2) 0.063(3) 0.0006(19) 0.013(2) 0.005(2)
C7 0.062(3) 0.067(3) 0.041(2) -0.0052(19) 0.0128(18) -0.006(2)
C4 0.048(2) 0.048(2) 0.050(2) 0.0003(17) 0.0104(18) 0.0025(19)
O1 0.068(2) 0.0504(19) 0.093(3) -0.0017(17) 0.0045(19) -0.0019(16)
C9 0.060(3) 0.065(3) 0.042(2) -0.0006(18) 0.0032(18) 0.004(2)
C8 0.055(3) 0.056(3) 0.047(2) -0.0048(18) 0.0118(17) -0.001(2)
C5 0.050(3) 0.049(2) 0.047(2) 0.0018(16) 0.0123(18) 0.0035(18)
C2 0.062(3) 0.049(2) 0.056(2) 0.0106(18) 0.013(2) 0.011(2)
C6 0.056(3) 0.056(3) 0.052(2) -0.0036(19) 0.0137(18) -0.005(2)
C10 0.064(3) 0.058(3) 0.046(2) 0.0068(18) 0.008(2) 0.009(2)
C12 0.107(5) 0.055(3) 0.103(5) -0.014(3) 0.028(4) -0.009(3)
C11 0.089(5) 0.048(3) 0.126(5) -0.011(3) 0.013(4) 0.005(3)

_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
Cl2 C7 1.727(5) . ?
Cl1 C2 1.727(4) . ?
N1 C4 1.361(6) . ?
N1 C1 1.370(6) . ?
N1 H1N 1.11(9) . ?
N2 C8 1.357(6) . ?
N2 C5 1.357(6) . ?
O2 C6 1.356(6) . ?
O2 C12 1.427(7) . ?
C1 C10 1.395(7) . ?
C1 C2 1.435(7) . ?
C3 C2 1.339(7) . ?
C3 O1 1.359(6) . ?
C3 C4 1.434(6) . ?
C7 C6 1.353(7) . ?
C7 C8 1.428(7) . ?
C4 C5 1.418(6) . ?
O1 C11 1.419(7) . ?
C9 C10 1.373(7) 3_665 ?
C9 C8 1.395(7) . ?
C9 H9 0.9300 . ?
C5 C6 1.437(6) . ?
C10 C9 1.373(7) 3_665 ?
C10 H10 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C4 N1 C1 109.0(4) . . ?
C4 N1 H1N 138(6) . . ?
C1 N1 H1N 113(6) . . ?
C8 N2 C5 109.7(4) . . ?
C6 O2 C12 114.9(4) . . ?
N1 C1 C10 127.4(4) . . ?
N1 C1 C2 106.5(4) . . ?
C10 C1 C2 126.0(4) . . ?
C2 C3 O1 128.1(4) . . ?
C2 C3 C4 106.6(4) . . ?
O1 C3 C4 125.1(5) . . ?
C6 C7 C8 109.3(4) . . ?
C6 C7 Cl2 126.2(4) . . ?
C8 C7 Cl2 124.5(4) . . ?
N1 C4 C5 119.7(4) . . ?
N1 C4 C3 108.5(4) . . ?
C5 C4 C3 131.8(4) . . ?
C3 O1 C11 116.2(5) . . ?
C10 C9 C8 131.1(4) 3_665 . ?
C10 C9 H9 114.5 3_665 . ?
C8 C9 H9 114.5 . . ?
N2 C8 C9 128.4(4) . . ?
N2 C8 C7 106.7(4) . . ?
C9 C8 C7 124.9(4) . . ?
N2 C5 C4 120.3(4) . . ?
N2 C5 C6 108.3(4) . . ?
C4 C5 C6 131.4(4) . . ?
C3 C2 C1 109.3(4) . . ?
C3 C2 Cl1 127.5(4) . . ?
C1 C2 Cl1 123.2(4) . . ?
C7 C6 O2 127.2(4) . . ?
C7 C6 C5 105.9(4) . . ?
O2 C6 C5 126.9(4) . . ?
C9 C10 C1 131.8(4) 3_665 . ?
C9 C10 H10 114.1 3_665 . ?
C1 C10 H10 114.1 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.120
####################################################################### 
# 
# 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_TCTMPoR
_database_code_depnum_ccdc_archive 'CCDC 1062098'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 3,6,13,16-tetrachloro-2,7,12,17-tetramethoxy-porphycene 
;
_chemical_name_common            porphycene
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Cl4 N4 O4'
_chemical_formula_sum            'C24 H18 Cl4 N4 O4'
_chemical_formula_weight         568.22

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   4.1263(3)
_cell_length_b                   23.8718(19)
_cell_length_c                   11.9867(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.803(5)
_cell_angle_gamma                90.00
_cell_volume                     1166.82(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    895
_cell_measurement_theta_min      4.1790
_cell_measurement_theta_max      70.7790

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    4.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5143
_exptl_absorpt_correction_T_max  0.6075
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4043
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         71.88
_reflns_number_total             2190
_reflns_number_gt                1355
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material  
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;

_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)+(0.1181P)²+0.7080P] 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         2190
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2632
_refine_ls_wR_factor_gt          0.2125
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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
Cl1 Cl 0.2238(4) 0.66821(8) 0.78099(13) 0.0800(6) Uani 1 1 d . . .
Cl2 Cl 1.6542(5) 0.29911(8) 0.96482(14) 0.0857(6) Uani 1 1 d . . .
O2 O 1.3807(12) 0.33859(19) 0.7220(3) 0.0713(12) Uani 1 1 d . . .
N1 N 0.7775(13) 0.5355(2) 0.8624(3) 0.0598(12) Uani 1 1 d . . .
O1 O 0.3871(11) 0.5855(2) 0.5955(3) 0.0741(13) Uani 1 1 d . . .
N2 N 1.1596(12) 0.4412(2) 0.9126(4) 0.0597(12) Uani 1 1 d . . .
C6 C 1.0035(15) 0.4433(3) 0.7038(4) 0.0620(15) Uani 1 1 d . . .
H6 H 1.0356 0.4225 0.6409 0.074 Uiso 1 1 calc R . .
C3 C 0.5085(15) 0.5779(3) 0.7074(5) 0.0614(15) Uani 1 1 d . . .
C1 C 0.6287(14) 0.5831(3) 0.8967(4) 0.0572(14) Uani 1 1 d . . .
C4 C 0.7091(15) 0.5315(3) 0.7471(4) 0.0617(15) Uani 1 1 d . . .
C8 C 1.3326(15) 0.3693(3) 0.8129(5) 0.0627(14) Uani 1 1 d . . .
C2 C 0.4572(14) 0.6092(3) 0.7961(5) 0.0612(14) Uani 1 1 d . . .
C9 C 1.4414(15) 0.3589(3) 0.9231(5) 0.0617(14) Uani 1 1 d . . .
C5 C 0.8163(15) 0.4907(3) 0.6789(4) 0.0662(16) Uani 1 1 d . . .
H5 H 0.7494 0.4965 0.6021 0.079 Uiso 1 1 calc R . .
C7 C 1.1541(15) 0.4209(3) 0.8065(5) 0.0606(14) Uani 1 1 d . . .
C10 C 1.3348(15) 0.4046(3) 0.9871(4) 0.0596(14) Uani 1 1 d . . .
C12 C 1.1775(18) 0.2902(3) 0.6996(6) 0.0790(19) Uani 1 1 d . . .
H12A H 1.2140 0.2653 0.7633 0.119 Uiso 1 1 calc R . .
H12B H 1.2307 0.2713 0.6341 0.119 Uiso 1 1 calc R . .
H12C H 0.9514 0.3013 0.6863 0.119 Uiso 1 1 calc R . .
C11 C 0.5361(19) 0.6296(4) 0.5426(5) 0.092(2) Uani 1 1 d . . .
H11A H 0.4925 0.6646 0.5768 0.138 Uiso 1 1 calc R . .
H11B H 0.4482 0.6305 0.4637 0.138 Uiso 1 1 calc R . .
H11C H 0.7687 0.6236 0.5514 0.138 Uiso 1 1 calc R . .
H1N H 0.99(3) 0.495(5) 0.920(7) 0.17(4) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0848(11) 0.0836(12) 0.0669(9) 0.0012(8) -0.0039(7) 0.0148(9)
Cl2 0.1084(14) 0.0814(12) 0.0664(9) -0.0005(8) 0.0111(9) 0.0226(10)
O2 0.088(3) 0.073(3) 0.056(2) -0.012(2) 0.021(2) -0.006(2)
N1 0.074(3) 0.064(3) 0.041(2) 0.001(2) 0.0060(19) -0.003(2)
O1 0.083(3) 0.086(3) 0.047(2) 0.008(2) -0.0067(19) -0.005(2)
N2 0.067(3) 0.064(3) 0.048(2) -0.001(2) 0.0075(19) -0.006(2)
C6 0.069(4) 0.073(4) 0.043(3) -0.006(2) 0.008(2) -0.005(3)
C3 0.064(3) 0.069(4) 0.048(3) 0.005(3) -0.001(2) -0.011(3)
C1 0.061(3) 0.063(3) 0.047(3) 0.002(2) 0.008(2) -0.008(3)
C4 0.067(3) 0.075(4) 0.041(3) 0.002(2) 0.003(2) -0.014(3)
C8 0.071(4) 0.066(4) 0.054(3) 0.000(3) 0.017(2) -0.001(3)
C2 0.059(3) 0.066(4) 0.056(3) 0.009(3) 0.000(2) -0.007(3)
C9 0.066(3) 0.064(4) 0.055(3) 0.002(3) 0.011(2) -0.007(3)
C5 0.074(4) 0.083(4) 0.039(3) 0.000(3) 0.001(2) 0.002(3)
C7 0.068(4) 0.063(4) 0.051(3) -0.004(2) 0.011(2) -0.013(3)
C10 0.065(3) 0.067(4) 0.046(3) 0.004(2) 0.008(2) -0.006(3)
C12 0.085(4) 0.078(5) 0.074(4) -0.022(3) 0.012(3) 0.000(4)
C11 0.099(5) 0.123(7) 0.049(3) 0.017(4) -0.002(3) -0.015(5)

_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 C2 1.701(7) . ?
Cl2 C9 1.709(7) . ?
O2 C8 1.353(7) . ?
O2 C12 1.429(8) . ?
N1 C4 1.371(6) . ?
N1 C1 1.384(8) . ?
O1 C3 1.369(6) . ?
O1 C11 1.418(8) . ?
N2 C7 1.358(7) . ?
N2 C10 1.372(7) . ?
C6 C5 1.377(9) . ?
C6 C7 1.398(8) . ?
C3 C2 1.342(9) . ?
C3 C4 1.422(9) . ?
C1 C10 1.409(7) 3_767 ?
C1 C2 1.442(7) . ?
C4 C5 1.386(9) . ?
C8 C9 1.351(8) . ?
C8 C7 1.431(9) . ?
C9 C10 1.442(8) . ?
C10 C1 1.409(7) 3_767 ?

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
C8 O2 C12 115.8(5) . . ?
C4 N1 C1 108.9(5) . . ?
C3 O1 C11 114.6(5) . . ?
C7 N2 C10 108.3(5) . . ?
C5 C6 C7 131.7(6) . . ?
C2 C3 O1 128.7(6) . . ?
C2 C3 C4 108.8(5) . . ?
O1 C3 C4 122.5(6) . . ?
N1 C1 C10 118.7(5) . 3_767 ?
N1 C1 C2 106.8(5) . . ?
C10 C1 C2 134.5(6) 3_767 . ?
N1 C4 C5 127.5(6) . . ?
N1 C4 C3 107.6(5) . . ?
C5 C4 C3 124.9(5) . . ?
C9 C8 O2 128.3(6) . . ?
C9 C8 C7 107.6(6) . . ?
O2 C8 C7 124.1(5) . . ?
C3 C2 C1 107.8(6) . . ?
C3 C2 Cl1 122.1(5) . . ?
C1 C2 Cl1 130.1(5) . . ?
C8 C9 C10 107.3(6) . . ?
C8 C9 Cl2 121.3(5) . . ?
C10 C9 Cl2 131.4(4) . . ?
C6 C5 C4 131.9(5) . . ?
N2 C7 C6 129.0(6) . . ?
N2 C7 C8 108.8(5) . . ?
C6 C7 C8 122.2(5) . . ?
N2 C10 C1 118.5(5) . 3_767 ?
N2 C10 C9 108.0(5) . . ?
C1 C10 C9 133.5(6) 3_767 . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        71.88
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_ZnTCTMPo.Py
_database_code_depnum_ccdc_archive 'CCDC 1062099'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            porphycene
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H21 Cl4 N5 O4 Zn'
_chemical_formula_weight         710.68

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   14.0391(19)
_cell_length_b                   14.1663(13)
_cell_length_c                   15.990(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.950(16)
_cell_angle_gamma                90.00
_cell_volume                     2906.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1218
_cell_measurement_theta_min      2.8810
_cell_measurement_theta_max      22.2200

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    1.259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10492
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_sigmaI/netI    0.1576
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         24.71
_reflns_number_total             4964
_reflns_number_gt                2576
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material  
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;

_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)+(0.0000P)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         4964
_refine_ls_number_parameters     392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_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
Zn1 Zn 0.51480(6) 0.32626(5) 0.20498(5) 0.0366(2) Uani 1 1 d . . .
Cl2 Cl 0.82671(14) 0.22130(12) 0.06024(14) 0.0626(6) Uani 1 1 d . . .
Cl3 Cl 0.24270(13) 0.22992(12) -0.17864(12) 0.0585(5) Uani 1 1 d . . .
Cl4 Cl 0.20177(15) 0.55506(13) 0.27658(15) 0.0740(6) Uani 1 1 d . . .
Cl1 Cl 0.78815(16) 0.57407(15) 0.50446(15) 0.0934(8) Uani 1 1 d . . .
O4 O 0.1202(3) 0.4515(3) 0.0849(3) 0.0560(14) Uani 1 1 d . . .
N3 N 0.4044(4) 0.3025(3) 0.0761(3) 0.0322(13) Uani 1 1 d . . .
N1 N 0.6242(4) 0.4134(3) 0.2971(3) 0.0354(13) Uani 1 1 d . . .
O3 O 0.1362(3) 0.3483(3) -0.0707(3) 0.0529(13) Uani 1 1 d . . .
N2 N 0.6337(4) 0.3125(3) 0.1631(4) 0.0383(14) Uani 1 1 d . . .
N4 N 0.3928(4) 0.4026(3) 0.2107(4) 0.0349(13) Uani 1 1 d . . .
C9 C 0.5827(5) 0.2147(4) 0.0237(4) 0.0359(16) Uani 1 1 d . . .
H9 H 0.6144 0.1746 -0.0034 0.043 Uiso 1 1 calc R . .
C13 C 0.2388(5) 0.3229(4) -0.0306(5) 0.0387(17) Uani 1 1 d . . .
C6 C 0.8067(5) 0.3285(4) 0.1935(5) 0.0425(18) Uani 1 1 d . . .
C19 C 0.4453(6) 0.5010(4) 0.3503(4) 0.0433(19) Uani 1 1 d . . .
H19 H 0.4136 0.5306 0.3843 0.052 Uiso 1 1 calc R . .
C8 C 0.6536(5) 0.2627(4) 0.0999(4) 0.0323(16) Uani 1 1 d . . .
C14 C 0.3097(5) 0.3405(4) 0.0618(4) 0.0327(16) Uani 1 1 d . . .
C16 C 0.2203(5) 0.4414(4) 0.1471(5) 0.0432(19) Uani 1 1 d . . .
C11 C 0.3963(5) 0.2602(4) -0.0027(4) 0.0322(16) Uani 1 1 d . . .
C4 C 0.7175(5) 0.4071(4) 0.2918(5) 0.0401(18) Uani 1 1 d . . .
O2 O 0.9063(3) 0.3602(3) 0.2324(3) 0.0568(14) Uani 1 1 d . . .
C18 C 0.3742(5) 0.4617(4) 0.2692(4) 0.0359(17) Uani 1 1 d . . .
C15 C 0.3031(5) 0.3909(4) 0.1350(5) 0.0355(17) Uani 1 1 d . . .
C29 C 0.4429(5) 0.1608(4) 0.2814(5) 0.051(2) Uani 1 1 d . . .
H29 H 0.3777 0.1786 0.2384 0.061 Uiso 1 1 calc R . .
C25 C 0.6192(6) 0.1791(4) 0.3449(5) 0.0497(19) Uani 1 1 d . . .
H25 H 0.6786 0.2098 0.3470 0.060 Uiso 1 1 calc R . .
O1 O 0.8949(4) 0.4709(3) 0.3814(4) 0.086(2) Uani 1 1 d . . .
C20 C 0.5534(5) 0.5054(4) 0.3914(4) 0.046(2) Uani 1 1 d . . .
H20 H 0.5786 0.5380 0.4466 0.056 Uiso 1 1 calc R . .
N5 N 0.5270(4) 0.2066(3) 0.2833(4) 0.0410(14) Uani 1 1 d . . .
C1 C 0.6327(6) 0.4712(4) 0.3673(5) 0.0422(18) Uani 1 1 d . . .
C17 C 0.2642(5) 0.4838(4) 0.2295(5) 0.0411(18) Uani 1 1 d . . .
C5 C 0.7238(5) 0.3531(4) 0.2208(5) 0.0364(17) Uani 1 1 d . . .
C10 C 0.4756(5) 0.2145(4) -0.0194(4) 0.0360(16) Uani 1 1 d . . .
H10 H 0.4504 0.1758 -0.0708 0.043 Uiso 1 1 calc R . .
C12 C 0.2919(5) 0.2717(4) -0.0678(4) 0.0365(17) Uani 1 1 d . . .
C3 C 0.7921(6) 0.4631(4) 0.3641(5) 0.050(2) Uani 1 1 d . . .
C7 C 0.7632(5) 0.2713(4) 0.1202(5) 0.0410(17) Uani 1 1 d . . .
C26 C 0.6302(7) 0.1074(5) 0.4052(5) 0.066(2) Uani 1 1 d . . .
H26 H 0.6964 0.0897 0.4465 0.080 Uiso 1 1 calc R . .
C2 C 0.7385(6) 0.5022(4) 0.4103(5) 0.055(2) Uani 1 1 d . . .
C21 C 0.9360(6) 0.5610(5) 0.3808(5) 0.090(3) Uani 1 1 d . . .
H21A H 0.8862 0.5978 0.3324 0.135 Uiso 1 1 calc R . .
H21B H 0.9990 0.5553 0.3712 0.135 Uiso 1 1 calc R . .
H21C H 0.9510 0.5915 0.4384 0.135 Uiso 1 1 calc R . .
C22 C 0.9744(5) 0.3011(5) 0.3028(5) 0.086(3) Uani 1 1 d . . .
H22A H 0.9480 0.2934 0.3491 0.129 Uiso 1 1 calc R . .
H22B H 1.0423 0.3293 0.3292 0.129 Uiso 1 1 calc R . .
H22C H 0.9790 0.2406 0.2776 0.129 Uiso 1 1 calc R . .
C27 C 0.5453(9) 0.0620(5) 0.4053(6) 0.077(3) Uani 1 1 d . . .
H27 H 0.5518 0.0147 0.4476 0.092 Uiso 1 1 calc R . .
C24 C 0.0538(5) 0.3737(5) 0.0823(5) 0.073(3) Uani 1 1 d . . .
H24A H 0.0900 0.3155 0.0850 0.110 Uiso 1 1 calc R . .
H24B H -0.0080 0.3760 0.0266 0.110 Uiso 1 1 calc R . .
H24C H 0.0350 0.3774 0.1336 0.110 Uiso 1 1 calc R . .
C23 C 0.1185(6) 0.4375(5) -0.1163(5) 0.083(3) Uani 1 1 d . . .
H23A H 0.1603 0.4849 -0.0746 0.124 Uiso 1 1 calc R . .
H23B H 0.0462 0.4540 -0.1372 0.124 Uiso 1 1 calc R . .
H23C H 0.1371 0.4335 -0.1677 0.124 Uiso 1 1 calc R . .
C28 C 0.4490(7) 0.0880(5) 0.3407(6) 0.072(3) Uani 1 1 d . . .
H28 H 0.3890 0.0570 0.3371 0.086 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0367(5) 0.0372(4) 0.0337(5) -0.0015(4) 0.0118(4) 0.0006(4)
Cl2 0.0485(12) 0.0784(13) 0.0704(15) -0.0060(11) 0.0338(11) 0.0085(10)
Cl3 0.0471(12) 0.0820(13) 0.0413(12) -0.0205(10) 0.0127(10) -0.0066(10)
Cl4 0.0674(14) 0.0828(13) 0.0807(17) -0.0253(12) 0.0391(13) 0.0159(11)
Cl1 0.0664(16) 0.1074(17) 0.0819(18) -0.0600(14) 0.0049(14) -0.0068(12)
O4 0.039(3) 0.059(3) 0.066(4) 0.000(3) 0.018(3) 0.009(3)
N3 0.029(3) 0.035(3) 0.031(3) -0.002(2) 0.010(3) 0.001(2)
N1 0.034(4) 0.037(3) 0.032(3) -0.008(3) 0.012(3) -0.002(3)
O3 0.029(3) 0.067(3) 0.050(3) -0.010(3) 0.003(3) 0.001(2)
N2 0.027(3) 0.042(3) 0.043(4) -0.007(3) 0.011(3) -0.003(3)
N4 0.040(4) 0.027(3) 0.039(4) -0.005(3) 0.017(3) -0.001(2)
C9 0.042(4) 0.037(4) 0.035(4) 0.005(3) 0.021(4) 0.007(3)
C13 0.034(4) 0.031(3) 0.045(5) 0.000(3) 0.010(4) -0.003(3)
C6 0.029(4) 0.039(4) 0.057(5) 0.007(4) 0.014(4) 0.004(3)
C19 0.068(6) 0.032(4) 0.036(5) -0.007(3) 0.028(4) -0.002(4)
C8 0.029(4) 0.035(4) 0.031(4) 0.005(3) 0.011(3) 0.009(3)
C14 0.030(4) 0.034(3) 0.030(4) 0.003(3) 0.009(3) -0.002(3)
C16 0.036(5) 0.034(4) 0.059(6) 0.008(4) 0.019(4) 0.005(3)
C11 0.029(4) 0.032(3) 0.035(4) -0.009(3) 0.012(3) -0.005(3)
C4 0.024(4) 0.038(4) 0.042(5) 0.008(3) -0.004(4) 0.000(3)
O2 0.024(3) 0.071(3) 0.067(4) 0.005(3) 0.010(3) -0.006(2)
C18 0.052(5) 0.029(3) 0.030(4) -0.002(3) 0.020(4) 0.002(3)
C15 0.035(4) 0.031(4) 0.039(5) -0.007(3) 0.014(4) -0.007(3)
C29 0.051(5) 0.046(4) 0.054(5) -0.015(4) 0.020(4) -0.009(4)
C25 0.054(5) 0.051(4) 0.040(5) -0.006(4) 0.015(4) 0.006(4)
O1 0.039(3) 0.085(4) 0.119(5) -0.051(4) 0.016(4) -0.014(3)
C20 0.056(5) 0.033(4) 0.034(5) -0.010(3) 0.002(4) 0.000(4)
N5 0.041(4) 0.040(3) 0.038(4) -0.009(3) 0.012(3) 0.000(3)
C1 0.047(5) 0.040(4) 0.035(5) -0.003(3) 0.011(4) -0.002(4)
C17 0.051(5) 0.028(3) 0.051(5) -0.005(3) 0.027(4) 0.002(3)
C5 0.031(4) 0.032(4) 0.044(5) -0.002(3) 0.013(4) 0.003(3)
C10 0.038(4) 0.033(3) 0.040(4) -0.006(3) 0.018(4) -0.010(3)
C12 0.032(4) 0.033(3) 0.042(4) -0.016(3) 0.012(4) -0.012(3)
C3 0.039(5) 0.047(4) 0.052(5) -0.009(4) 0.005(4) 0.007(4)
C7 0.041(4) 0.042(4) 0.040(5) 0.004(4) 0.017(4) 0.008(3)
C26 0.111(8) 0.049(5) 0.041(5) 0.011(4) 0.032(5) 0.027(5)
C2 0.051(5) 0.042(4) 0.049(5) -0.013(4) -0.003(4) -0.004(4)
C21 0.057(6) 0.112(7) 0.096(8) -0.004(6) 0.024(6) -0.035(5)
C22 0.033(5) 0.094(6) 0.099(8) -0.008(5) -0.007(5) 0.011(4)
C27 0.157(10) 0.040(5) 0.057(6) 0.016(4) 0.066(7) 0.016(6)
C24 0.041(5) 0.093(6) 0.091(7) 0.002(5) 0.031(5) -0.019(4)
C23 0.078(7) 0.088(6) 0.069(7) 0.020(5) 0.016(5) 0.039(5)
C28 0.124(9) 0.039(5) 0.074(7) -0.009(4) 0.062(7) -0.014(5)

_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
Zn1 N3 2.042(5) . ?
Zn1 N2 2.044(5) . ?
Zn1 N1 2.054(5) . ?
Zn1 N4 2.059(5) . ?
Zn1 N5 2.073(5) . ?
Cl2 C7 1.706(7) . ?
Cl3 C12 1.724(6) . ?
Cl4 C17 1.700(6) . ?
Cl1 C2 1.714(7) . ?
O4 C16 1.360(7) . ?
O4 C24 1.433(6) . ?
N3 C11 1.357(7) . ?
N3 C14 1.365(7) . ?
N1 C4 1.350(7) . ?
N1 C1 1.354(7) . ?
O3 C13 1.365(7) . ?
O3 C23 1.430(7) . ?
N2 C8 1.352(7) . ?
N2 C5 1.355(7) . ?
N4 C18 1.357(7) . ?
N4 C15 1.358(7) . ?
C9 C10 1.376(7) . ?
C9 C8 1.397(7) . ?
C13 C12 1.341(8) . ?
C13 C14 1.429(8) . ?
C6 C7 1.350(8) . ?
C6 O2 1.355(7) . ?
C6 C5 1.442(8) . ?
C19 C20 1.390(8) . ?
C19 C18 1.392(8) . ?
C8 C7 1.442(8) . ?
C14 C15 1.405(8) . ?
C16 C17 1.348(8) . ?
C16 C15 1.444(8) . ?
C11 C10 1.405(7) . ?
C11 C12 1.422(7) . ?
C4 C5 1.401(8) . ?
C4 C3 1.442(8) . ?
O2 C22 1.416(7) . ?
C18 C17 1.445(8) . ?
C29 N5 1.337(7) . ?
C29 C28 1.379(9) . ?
C25 N5 1.327(7) . ?
C25 C26 1.365(8) . ?
O1 C3 1.359(8) . ?
O1 C21 1.402(7) . ?
C20 C1 1.404(8) . ?
C1 C2 1.429(8) . ?
C3 C2 1.368(9) . ?
C26 C27 1.356(10) . ?
C27 C28 1.377(10) . ?

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
N3 Zn1 N2 92.3(2) . . ?
N3 Zn1 N1 149.71(18) . . ?
N2 Zn1 N1 79.6(2) . . ?
N3 Zn1 N4 80.1(2) . . ?
N2 Zn1 N4 150.36(19) . . ?
N1 Zn1 N4 92.6(2) . . ?
N3 Zn1 N5 108.52(19) . . ?
N2 Zn1 N5 104.0(2) . . ?
N1 Zn1 N5 101.8(2) . . ?
N4 Zn1 N5 105.6(2) . . ?
C16 O4 C24 114.0(5) . . ?
C11 N3 C14 108.1(5) . . ?
C11 N3 Zn1 138.8(4) . . ?
C14 N3 Zn1 113.1(4) . . ?
C4 N1 C1 109.3(6) . . ?
C4 N1 Zn1 112.1(4) . . ?
C1 N1 Zn1 138.3(5) . . ?
C13 O3 C23 113.8(5) . . ?
C8 N2 C5 108.1(5) . . ?
C8 N2 Zn1 137.7(4) . . ?
C5 N2 Zn1 113.4(4) . . ?
C18 N4 C15 108.7(5) . . ?
C18 N4 Zn1 138.7(4) . . ?
C15 N4 Zn1 112.5(4) . . ?
C10 C9 C8 133.2(6) . . ?
C12 C13 O3 127.2(6) . . ?
C12 C13 C14 105.9(6) . . ?
O3 C13 C14 126.8(6) . . ?
C7 C6 O2 128.1(7) . . ?
C7 C6 C5 105.7(6) . . ?
O2 C6 C5 126.2(6) . . ?
C20 C19 C18 133.7(7) . . ?
N2 C8 C9 127.9(6) . . ?
N2 C8 C7 108.3(5) . . ?
C9 C8 C7 123.7(6) . . ?
N3 C14 C15 116.7(6) . . ?
N3 C14 C13 109.1(6) . . ?
C15 C14 C13 134.1(6) . . ?
C17 C16 O4 126.5(6) . . ?
C17 C16 C15 106.1(6) . . ?
O4 C16 C15 127.2(7) . . ?
N3 C11 C10 127.3(6) . . ?
N3 C11 C12 107.6(5) . . ?
C10 C11 C12 125.1(6) . . ?
N1 C4 C5 118.0(6) . . ?
N1 C4 C3 108.7(6) . . ?
C5 C4 C3 133.3(7) . . ?
C6 O2 C22 114.0(5) . . ?
N4 C18 C19 128.5(6) . . ?
N4 C18 C17 107.6(5) . . ?
C19 C18 C17 123.8(6) . . ?
N4 C15 C14 117.0(6) . . ?
N4 C15 C16 109.0(6) . . ?
C14 C15 C16 133.8(6) . . ?
N5 C29 C28 122.7(7) . . ?
N5 C25 C26 122.6(7) . . ?
C3 O1 C21 118.6(6) . . ?
C19 C20 C1 133.7(6) . . ?
C25 N5 C29 117.4(6) . . ?
C25 N5 Zn1 120.3(5) . . ?
C29 N5 Zn1 121.9(5) . . ?
N1 C1 C20 128.5(6) . . ?
N1 C1 C2 108.0(6) . . ?
C20 C1 C2 123.2(6) . . ?
C16 C17 C18 108.5(6) . . ?
C16 C17 Cl4 125.7(6) . . ?
C18 C17 Cl4 125.8(5) . . ?
N2 C5 C4 115.8(6) . . ?
N2 C5 C6 109.7(6) . . ?
C4 C5 C6 134.5(6) . . ?
C9 C10 C11 133.9(6) . . ?
C13 C12 C11 109.3(6) . . ?
C13 C12 Cl3 125.4(5) . . ?
C11 C12 Cl3 125.3(5) . . ?
O1 C3 C2 128.9(7) . . ?
O1 C3 C4 125.0(7) . . ?
C2 C3 C4 106.0(6) . . ?
C6 C7 C8 108.2(6) . . ?
C6 C7 Cl2 125.5(5) . . ?
C8 C7 Cl2 126.3(5) . . ?
C27 C26 C25 120.4(8) . . ?
C3 C2 C1 107.9(6) . . ?
C3 C2 Cl1 126.7(6) . . ?
C1 C2 Cl1 125.3(6) . . ?
C26 C27 C28 118.0(8) . . ?
C27 C28 C29 118.9(8) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.083
####################################################################### 
# 
# 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_ZnTCTMPoR.Py
_database_code_depnum_ccdc_archive 'CCDC 1062100'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            porphycene
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H21 Cl4 N5 O4 Zn'
_chemical_formula_sum            'C29 H21 Cl4 N5 O4 Zn'
_chemical_formula_weight         710.68

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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   10.7037(5)
_cell_length_b                   17.9473(9)
_cell_length_c                   15.8353(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.927(5)
_cell_angle_gamma                90.00
_cell_volume                     2910.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3243
_cell_measurement_theta_min      2.5410
_cell_measurement_theta_max      71.2520

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    4.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.459
_exptl_absorpt_correction_T_max  0.554
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11867
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         71.91
_reflns_number_total             5521
_reflns_number_gt                3903
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material  
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;

_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)+(0.0781P)²+0.8540P] 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         5521
_refine_ls_number_parameters     392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1617
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
Zn1 Zn 0.14892(4) 0.00196(3) 0.73960(3) 0.05189(17) Uani 1 1 d . . .
Cl1 Cl -0.38206(11) -0.07339(9) 0.56650(9) 0.0869(4) Uani 1 1 d . . .
Cl2 Cl -0.30550(12) 0.05462(9) 0.45433(9) 0.0924(4) Uani 1 1 d . . .
Cl4 Cl 0.62533(14) -0.08764(13) 0.98245(11) 0.1199(6) Uani 1 1 d . . .
Cl3 Cl 0.70163(13) 0.03963(12) 0.86965(14) 0.1236(7) Uani 1 1 d . . .
N1 N -0.0124(3) -0.06470(18) 0.7095(2) 0.0533(7) Uani 1 1 d . . .
N4 N 0.2679(3) -0.0719(2) 0.8241(2) 0.0586(8) Uani 1 1 d . . .
N2 N 0.0444(3) 0.04875(19) 0.6242(2) 0.0533(7) Uani 1 1 d . . .
C4 C -0.1118(4) -0.0370(2) 0.6412(3) 0.0548(9) Uani 1 1 d . . .
C5 C -0.0796(4) 0.0233(2) 0.5943(2) 0.0520(9) Uani 1 1 d . . .
O1 O -0.2684(3) -0.18835(17) 0.7191(2) 0.0747(9) Uani 1 1 d . . .
N3 N 0.3256(3) 0.0426(2) 0.7400(2) 0.0582(8) Uani 1 1 d . . .
N5 N 0.1015(3) 0.07559(18) 0.8292(2) 0.0519(7) Uani 1 1 d . . .
C7 C -0.0611(4) 0.1186(2) 0.5049(3) 0.0603(10) Uani 1 1 d . . .
C8 C 0.0603(4) 0.1056(2) 0.5722(3) 0.0572(9) Uani 1 1 d . . .
C6 C -0.1475(4) 0.0669(2) 0.5187(3) 0.0581(9) Uani 1 1 d . . .
C3 C -0.2265(4) -0.0812(2) 0.6366(3) 0.0578(9) Uani 1 1 d . . .
C14 C 0.4273(4) 0.0108(3) 0.8031(3) 0.0636(11) Uani 1 1 d . . .
C20 C 0.0115(4) -0.1678(2) 0.8177(3) 0.0635(10) Uani 1 1 d . . .
H20 H -0.0416 -0.2034 0.8327 0.076 Uiso 1 1 calc R . .
C16 C 0.4653(4) -0.0965(3) 0.9217(3) 0.0736(13) Uani 1 1 d . . .
C10 C 0.3016(4) 0.1447(3) 0.6309(3) 0.0659(11) Uani 1 1 d . . .
H10 H 0.3537 0.1815 0.6170 0.079 Uiso 1 1 calc R . .
O2 O -0.0686(4) 0.1721(2) 0.4446(2) 0.0883(11) Uani 1 1 d . . .
C19 C 0.1395(5) -0.1717(3) 0.8701(3) 0.0668(11) Uani 1 1 d . . .
H19 H 0.1540 -0.2097 0.9116 0.080 Uiso 1 1 calc R . .
C9 C 0.1737(4) 0.1471(3) 0.5776(3) 0.0642(10) Uani 1 1 d . . .
H9 H 0.1595 0.1849 0.5356 0.077 Uiso 1 1 calc R . .
C15 C 0.3963(4) -0.0501(3) 0.8498(3) 0.0623(10) Uani 1 1 d . . .
C1 C -0.0567(4) -0.1227(2) 0.7471(3) 0.0575(9) Uani 1 1 d . . .
O3 O 0.5839(3) 0.1595(2) 0.7196(3) 0.1000(13) Uani 1 1 d . . .
C2 C -0.1926(4) -0.1325(2) 0.7015(3) 0.0594(10) Uani 1 1 d . . .
C11 C 0.3701(4) 0.0994(3) 0.7010(3) 0.0634(10) Uani 1 1 d . . .
C12 C 0.5095(4) 0.1050(3) 0.7410(4) 0.0741(13) Uani 1 1 d . . .
C13 C 0.5435(4) 0.0515(3) 0.8030(3) 0.0735(13) Uani 1 1 d . . .
C25 C 0.1231(5) 0.1480(2) 0.8281(3) 0.0666(11) Uani 1 1 d . . .
H25 H 0.1585 0.1672 0.7856 0.080 Uiso 1 1 calc R . .
C29 C 0.0550(5) 0.0497(3) 0.8917(3) 0.0713(12) Uani 1 1 d . . .
H29 H 0.0409 -0.0014 0.8936 0.086 Uiso 1 1 calc R . .
C28 C 0.0263(5) 0.0940(3) 0.9542(3) 0.0765(13) Uani 1 1 d . . .
H28 H -0.0070 0.0734 0.9970 0.092 Uiso 1 1 calc R . .
C18 C 0.2527(4) -0.1301(3) 0.8739(3) 0.0639(11) Uani 1 1 d . . .
O4 O 0.3871(4) -0.2017(3) 0.9957(3) 0.1146(15) Uani 1 1 d . . .
C17 C 0.3776(5) -0.1463(3) 0.9364(3) 0.0773(13) Uani 1 1 d . . .
C27 C 0.0472(5) 0.1683(3) 0.9524(3) 0.0708(12) Uani 1 1 d . . .
H27 H 0.0295 0.1998 0.9942 0.085 Uiso 1 1 calc R . .
C26 C 0.0951(6) 0.1956(3) 0.8876(3) 0.0809(15) Uani 1 1 d . . .
H26 H 0.1087 0.2465 0.8838 0.097 Uiso 1 1 calc R . .
C22 C -0.1843(5) 0.1897(4) 0.3808(4) 0.0934(17) Uani 1 1 d . . .
H22A H -0.2175 0.1463 0.3462 0.140 Uiso 1 1 calc R . .
H22B H -0.1683 0.2282 0.3432 0.140 Uiso 1 1 calc R . .
H22C H -0.2473 0.2069 0.4089 0.140 Uiso 1 1 calc R . .
C21 C -0.3591(6) -0.1651(4) 0.7644(5) 0.105(2) Uani 1 1 d . . .
H21A H -0.3128 -0.1416 0.8190 0.158 Uiso 1 1 calc R . .
H21B H -0.4055 -0.2077 0.7764 0.158 Uiso 1 1 calc R . .
H21C H -0.4200 -0.1304 0.7283 0.158 Uiso 1 1 calc R . .
C23 C 0.6787(7) 0.1368(5) 0.6807(6) 0.137(3) Uani 1 1 d . . .
H23A H 0.7456 0.1095 0.7230 0.205 Uiso 1 1 calc R . .
H23B H 0.7165 0.1797 0.6615 0.205 Uiso 1 1 calc R . .
H23C H 0.6394 0.1055 0.6309 0.205 Uiso 1 1 calc R . .
C24 C 0.5000(7) -0.2254(5) 1.0501(6) 0.152(4) Uani 1 1 d . . .
H24A H 0.5567 -0.2409 1.0163 0.228 Uiso 1 1 calc R . .
H24B H 0.4842 -0.2667 1.0841 0.228 Uiso 1 1 calc R . .
H24C H 0.5405 -0.1857 1.0891 0.228 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0418(3) 0.0564(3) 0.0554(3) -0.0024(2) 0.0109(2) 0.0014(2)
Cl1 0.0486(6) 0.1034(9) 0.0969(9) 0.0104(7) 0.0026(5) -0.0141(6)
Cl2 0.0618(7) 0.1057(10) 0.0885(8) 0.0179(7) -0.0116(6) -0.0120(6)
Cl4 0.0604(8) 0.1755(18) 0.1009(10) 0.0283(11) -0.0125(7) 0.0066(9)
Cl3 0.0458(6) 0.1370(14) 0.1648(16) 0.0162(13) -0.0060(8) -0.0052(8)
N1 0.0475(16) 0.0525(17) 0.0583(18) -0.0011(15) 0.0128(14) -0.0010(13)
N4 0.0482(17) 0.061(2) 0.0608(19) -0.0029(16) 0.0073(14) 0.0066(14)
N2 0.0437(16) 0.0602(19) 0.0539(17) -0.0014(15) 0.0111(13) -0.0001(13)
C4 0.0442(19) 0.059(2) 0.058(2) -0.0097(18) 0.0089(16) 0.0008(16)
C5 0.0465(19) 0.059(2) 0.0487(19) -0.0103(17) 0.0110(15) 0.0029(16)
O1 0.0684(19) 0.0573(17) 0.102(2) -0.0036(17) 0.0306(17) -0.0135(14)
N3 0.0440(16) 0.070(2) 0.0600(19) -0.0004(17) 0.0151(14) 0.0011(15)
N5 0.0452(16) 0.0545(18) 0.0556(17) -0.0017(15) 0.0143(13) -0.0017(13)
C7 0.060(2) 0.063(2) 0.056(2) 0.000(2) 0.0155(18) 0.0010(19)
C8 0.055(2) 0.062(2) 0.056(2) -0.0001(19) 0.0181(17) 0.0030(18)
C6 0.052(2) 0.061(2) 0.055(2) -0.0037(19) 0.0042(17) 0.0055(17)
C3 0.047(2) 0.060(2) 0.065(2) -0.008(2) 0.0135(17) -0.0053(17)
C14 0.0421(19) 0.075(3) 0.071(3) -0.013(2) 0.0115(18) 0.0058(18)
C20 0.066(3) 0.057(2) 0.069(3) -0.001(2) 0.022(2) -0.0032(19)
C16 0.051(2) 0.095(3) 0.067(3) -0.006(3) 0.004(2) 0.015(2)
C10 0.056(2) 0.068(3) 0.080(3) -0.004(2) 0.030(2) -0.010(2)
O2 0.082(2) 0.090(2) 0.081(2) 0.032(2) 0.0046(18) -0.0040(19)
C19 0.073(3) 0.059(2) 0.067(3) 0.008(2) 0.018(2) 0.011(2)
C9 0.061(2) 0.065(2) 0.069(3) 0.006(2) 0.023(2) -0.0030(19)
C15 0.046(2) 0.076(3) 0.062(2) -0.011(2) 0.0098(17) 0.0113(19)
C1 0.054(2) 0.052(2) 0.067(2) -0.0037(19) 0.0189(18) 0.0009(16)
O3 0.061(2) 0.093(3) 0.153(4) -0.005(3) 0.042(2) -0.0162(19)
C2 0.057(2) 0.050(2) 0.074(3) -0.012(2) 0.0223(19) -0.0081(17)
C11 0.049(2) 0.072(3) 0.070(3) -0.006(2) 0.0196(19) -0.0016(19)
C12 0.050(2) 0.079(3) 0.095(3) -0.016(3) 0.024(2) -0.008(2)
C13 0.043(2) 0.082(3) 0.091(3) -0.012(3) 0.012(2) 0.002(2)
C25 0.083(3) 0.056(2) 0.068(3) 0.002(2) 0.034(2) -0.003(2)
C29 0.089(3) 0.055(2) 0.080(3) -0.009(2) 0.042(3) -0.015(2)
C28 0.092(3) 0.072(3) 0.079(3) -0.001(3) 0.048(3) -0.014(3)
C18 0.060(2) 0.066(3) 0.061(2) -0.002(2) 0.0109(19) 0.0128(19)
O4 0.092(3) 0.132(4) 0.103(3) 0.056(3) 0.002(2) 0.022(3)
C17 0.069(3) 0.088(3) 0.067(3) 0.007(3) 0.007(2) 0.017(3)
C27 0.082(3) 0.064(3) 0.072(3) -0.007(2) 0.032(2) 0.005(2)
C26 0.122(4) 0.053(2) 0.082(3) 0.002(2) 0.050(3) 0.001(3)
C22 0.084(4) 0.105(4) 0.077(3) 0.022(3) 0.000(3) -0.004(3)
C21 0.112(5) 0.091(4) 0.138(6) -0.007(4) 0.078(5) -0.015(4)
C23 0.117(6) 0.128(6) 0.201(9) -0.002(6) 0.104(6) -0.017(5)
C24 0.107(6) 0.143(7) 0.184(8) 0.084(7) 0.007(5) 0.033(5)

_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
Zn1 N3 2.026(3) . ?
Zn1 N2 2.026(3) . ?
Zn1 N1 2.039(3) . ?
Zn1 N4 2.043(3) . ?
Zn1 N5 2.107(3) . ?
Cl1 C3 1.717(4) . ?
Cl2 C6 1.716(4) . ?
Cl4 C16 1.710(5) . ?
Cl3 C13 1.727(5) . ?
N1 C1 1.353(5) . ?
N1 C4 1.371(5) . ?
N4 C18 1.348(6) . ?
N4 C15 1.372(5) . ?
N2 C5 1.352(5) . ?
N2 C8 1.353(5) . ?
C4 C5 1.410(6) . ?
C4 C3 1.446(5) . ?
C5 C6 1.437(6) . ?
O1 C2 1.368(5) . ?
O1 C21 1.427(6) . ?
N3 C11 1.349(6) . ?
N3 C14 1.370(5) . ?
N5 C29 1.315(5) . ?
N5 C25 1.321(5) . ?
C7 O2 1.339(5) . ?
C7 C6 1.372(6) . ?
C7 C8 1.439(6) . ?
C8 C9 1.406(6) . ?
C3 C2 1.348(6) . ?
C14 C15 1.413(7) . ?
C14 C13 1.442(6) . ?
C20 C19 1.381(6) . ?
C20 C1 1.401(6) . ?
C16 C17 1.364(8) . ?
C16 C15 1.430(6) . ?
C10 C9 1.385(6) . ?
C10 C11 1.398(7) . ?
O2 C22 1.389(6) . ?
C19 C18 1.409(6) . ?
C1 C2 1.434(6) . ?
O3 C12 1.365(6) . ?
O3 C23 1.392(7) . ?
C11 C12 1.444(6) . ?
C12 C13 1.347(7) . ?
C25 C26 1.368(6) . ?
C29 C28 1.373(6) . ?
C28 C27 1.354(7) . ?
C18 C17 1.443(6) . ?
O4 C24 1.333(7) . ?
O4 C17 1.352(7) . ?
C27 C26 1.366(6) . ?

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
N3 Zn1 N2 97.10(14) . . ?
N3 Zn1 N1 159.74(14) . . ?
N2 Zn1 N1 79.91(13) . . ?
N3 Zn1 N4 80.11(14) . . ?
N2 Zn1 N4 159.16(13) . . ?
N1 Zn1 N4 95.53(14) . . ?
N3 Zn1 N5 100.36(13) . . ?
N2 Zn1 N5 99.75(13) . . ?
N1 Zn1 N5 99.89(12) . . ?
N4 Zn1 N5 101.06(13) . . ?
C1 N1 C4 109.6(3) . . ?
C1 N1 Zn1 136.9(3) . . ?
C4 N1 Zn1 112.4(3) . . ?
C18 N4 C15 109.1(4) . . ?
C18 N4 Zn1 136.7(3) . . ?
C15 N4 Zn1 113.0(3) . . ?
C5 N2 C8 109.0(3) . . ?
C5 N2 Zn1 113.8(3) . . ?
C8 N2 Zn1 136.7(3) . . ?
N1 C4 C5 116.2(3) . . ?
N1 C4 C3 107.1(4) . . ?
C5 C4 C3 136.7(4) . . ?
N2 C5 C4 116.1(3) . . ?
N2 C5 C6 108.3(4) . . ?
C4 C5 C6 135.6(4) . . ?
C2 O1 C21 114.8(4) . . ?
C11 N3 C14 109.7(4) . . ?
C11 N3 Zn1 136.5(3) . . ?
C14 N3 Zn1 113.3(3) . . ?
C29 N5 C25 117.7(4) . . ?
C29 N5 Zn1 120.2(3) . . ?
C25 N5 Zn1 122.0(3) . . ?
O2 C7 C6 134.1(4) . . ?
O2 C7 C8 119.8(4) . . ?
C6 C7 C8 106.1(4) . . ?
N2 C8 C9 128.5(4) . . ?
N2 C8 C7 109.1(4) . . ?
C9 C8 C7 122.4(4) . . ?
C7 C6 C5 107.5(4) . . ?
C7 C6 Cl2 125.8(3) . . ?
C5 C6 Cl2 126.6(3) . . ?
C2 C3 C4 107.5(4) . . ?
C2 C3 Cl1 123.0(3) . . ?
C4 C3 Cl1 129.6(3) . . ?
N3 C14 C15 116.5(4) . . ?
N3 C14 C13 106.9(4) . . ?
C15 C14 C13 136.6(4) . . ?
C19 C20 C1 134.7(4) . . ?
C17 C16 C15 107.2(4) . . ?
C17 C16 Cl4 126.2(4) . . ?
C15 C16 Cl4 126.5(4) . . ?
C9 C10 C11 134.4(4) . . ?
C7 O2 C22 122.5(4) . . ?
C20 C19 C18 133.6(4) . . ?
C10 C9 C8 134.7(4) . . ?
N4 C15 C14 115.6(4) . . ?
N4 C15 C16 108.2(4) . . ?
C14 C15 C16 136.2(4) . . ?
N1 C1 C20 128.9(4) . . ?
N1 C1 C2 107.9(4) . . ?
C20 C1 C2 123.2(4) . . ?
C12 O3 C23 117.0(5) . . ?
C3 C2 O1 127.7(4) . . ?
C3 C2 C1 108.0(4) . . ?
O1 C2 C1 124.2(4) . . ?
N3 C11 C10 129.0(4) . . ?
N3 C11 C12 108.0(4) . . ?
C10 C11 C12 122.9(4) . . ?
C13 C12 O3 129.7(5) . . ?
C13 C12 C11 107.2(4) . . ?
O3 C12 C11 122.9(5) . . ?
C12 C13 C14 108.2(4) . . ?
C12 C13 Cl3 122.8(4) . . ?
C14 C13 Cl3 129.0(4) . . ?
N5 C25 C26 122.1(4) . . ?
N5 C29 C28 123.4(4) . . ?
C27 C28 C29 118.9(4) . . ?
N4 C18 C19 129.3(4) . . ?
N4 C18 C17 108.2(4) . . ?
C19 C18 C17 122.5(5) . . ?
C24 O4 C17 123.6(6) . . ?
O4 C17 C16 133.2(5) . . ?
O4 C17 C18 119.4(5) . . ?
C16 C17 C18 107.3(5) . . ?
C28 C27 C26 118.0(5) . . ?
C27 C26 C25 119.9(5) . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        71.91
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.062
