#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/75/7117534.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7117534
loop_
_publ_author_name
'Anup Rana'
'Pradeepta K. Panda'
_publ_section_title
;
 Beta-Tetrachlorotetramethoxyporphycenes: positional effect of
 substituents on structure and photophysical properties
;
_journal_name_full               Chem.Commun.
_journal_page_first              12239
_journal_paper_doi               10.1039/C5cc03867G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C24 H18 Cl4 N4 O4'
_chemical_formula_sum            'C24 H18 Cl4 N4 O4'
_chemical_formula_weight         568.22
_chemical_name_common            porphycene
_chemical_name_systematic
; 
 2,7,12,17-tetrachloro-3,6,13,16-tetramethoxy-porphycene 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.544(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.9469(2)
_cell_length_b                   27.0301(15)
_cell_length_c                   10.9065(5)
_cell_measurement_reflns_used    1472
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.7320
_cell_measurement_theta_min      4.4670
_cell_volume                     1150.65(10)
_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_collection
;
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_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
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3733
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         4.41
_exptl_absorpt_coefficient_mu    5.047
_exptl_absorpt_correction_T_max  0.603
_exptl_absorpt_correction_T_min  0.492
_exptl_absorpt_correction_type   multi-scan
_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_crystal_colour            purple
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0744
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1953P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2148
_refine_ls_wR_factor_ref         0.2799
_reflns_number_gt                1455
_reflns_number_total             1961
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc03867g2.cif
_cod_data_source_block           TCTMPo
_cod_original_cell_volume        1150.65(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7117534
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'
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_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'
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
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 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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 .
