#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:33:36 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179976 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/70/7027062.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7027062
loop_
_publ_author_name
'Senge, Mathias O.'
'Gerstung, Vanessa'
'Ruhlandt-Senge, Karin'
'Runge, Steffen'
'Lehmann, Ingo'
_publ_section_title
;
 Non-planar porphyrins with mixed substituent pattern: bromination and
 formylation of ethyl-substituted tetraphenylporphyrins and
 tetraalkylporphyrins
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              4187
_journal_paper_doi               10.1039/a806460a
_journal_year                    1998
_chemical_formula_sum            'C44 H28 Br2 N4'
_chemical_formula_weight         772.52
_chemical_name_common            2,12-DiBr-TPP
_chemical_name_systematic
; 
 2,12-Dibromo-5,10,15,20-tetraphenylporphyrin 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.41(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.993(15)
_cell_length_b                   6.699(5)
_cell_length_c                   18.832(17)
_cell_measurement_reflns_used    37
_cell_measurement_temperature    129(2)
_cell_measurement_theta_max      52
_cell_measurement_theta_min      41
_cell_volume                     1736(3)
_computing_cell_refinement       'Siemens P3'
_computing_data_collection       'Siemens P3'
_computing_data_reduction        'XDISK, Shelxtl-Plus, Siemens, 1994'
_computing_molecular_graphics    'XP, Shelxtl-Plus, Siemens, 1994'
_computing_publication_material  'XCIF, Shelxtl-Plus, Siemens, 1994'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      129(2)
_diffrn_detector_area_resol_mean n/a
_diffrn_measured_fraction_theta_full 0.901
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'Syntex P21'
_diffrn_measurement_method       2theta-theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1280
_diffrn_reflns_av_sigmaI/netI    0.0716
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2691
_diffrn_reflns_theta_full        56.84
_diffrn_reflns_theta_max         56.84
_diffrn_reflns_theta_min         4.77
_diffrn_standards_decay_%        stable
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    3.256
_exptl_absorpt_correction_T_max  0.7366
_exptl_absorpt_correction_T_min  0.2928
_exptl_absorpt_correction_type   'empirical, XABS2'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       n/d
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2321
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.1102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1272P)²+19.5854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2638
_refine_ls_wR_factor_ref         0.2771
_reflns_number_gt                1875
_reflns_number_total             2321
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            806460asup1.cif
_cod_data_source_block           ms400
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/d' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1272P)^2^+19.5854P] where P=(Fo^2^+2Fc^2^)/3'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1272P)^2^+19.5854P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7027062
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'
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_calc_flag
_atom_site_refinement_flags
N21 N 0.8868(5) 0.7942(13) 0.9776(4) 0.030(2) Uani 1 d D
H21 H 0.9336 0.8835 0.9867 0.036 Uiso 1 calc R
N22 N 1.0804(5) 0.8415(13) 0.9352(5) 0.031(2) Uani 1 d D
H22 H 1.0537 0.8922 0.9701 0.037 Uiso 1 calc R
C1 C 0.8037(6) 0.7902(14) 1.0061(5) 0.028(2) Uani 1 d D
C2 C 0.7461(6) 0.6208(14) 0.9786(5) 0.030(2) Uani 1 d D
C3 C 0.7982(6) 0.5206(14) 0.9351(6) 0.036(3) Uani 1 d D
C4 C 0.8839(6) 0.6352(14) 0.9327(5) 0.030(2) Uani 1 d D
C5 C 0.9537(6) 0.5879(15) 0.8902(6) 0.030(3) Uani 1 d D
C6 C 1.0419(6) 0.6856(15) 0.8915(5) 0.028(2) Uani 1 d D
C7 C 1.1087(7) 0.6485(16) 0.8447(6) 0.034(3) Uani 1 d D
H7 H 1.1022 0.5473 0.8088 0.041 Uiso 1 calc R
C8 C 1.1847(7) 0.7822(15) 0.8594(6) 0.038(3) Uani 1 d D
C9 C 1.1661(6) 0.9076(15) 0.9173(5) 0.030(3) Uani 1 d D
C10 C 1.2214(7) 1.0717(15) 0.9443(6) 0.029(2) Uani 1 d D
Br1 Br 0.61708(17) 0.5411(4) 0.98217(14) 0.0190(7) Uani 0.36 d PD
Br2 Br 0.75773(11) 0.2632(2) 0.89828(8) 0.0146(5) Uani 0.56 d PD
Br3 Br 1.2925(13) 0.781(3) 0.8091(12) 0.068(6) Uani 0.08 d PD
C51 C 0.9300(5) 0.4355(9) 0.8328(3) 0.027(2) Uiso 1 d G
C52 C 0.8621(4) 0.4789(8) 0.7712(3) 0.034(3) Uiso 1 d G
H52 H 0.8295 0.6039 0.7670 0.040 Uiso 1 calc R
C53 C 0.8419(5) 0.3394(10) 0.7159(3) 0.036(3) Uiso 1 d G
H53 H 0.7955 0.3691 0.6739 0.044 Uiso 1 calc R
C54 C 0.8896(5) 0.1565(9) 0.7221(3) 0.044(3) Uiso 1 d G
H54 H 0.8758 0.0612 0.6843 0.053 Uiso 1 calc R
C55 C 0.9575(5) 0.1131(8) 0.7837(4) 0.041(3) Uiso 1 d G
H55 H 0.9901 -0.0119 0.7879 0.049 Uiso 1 calc R
C56 C 0.9777(4) 0.2526(9) 0.8390(3) 0.034(3) Uiso 1 d G
H56 H 1.0242 0.2230 0.8810 0.041 Uiso 1 calc R
C101 C 1.3099(4) 1.1088(11) 0.9123(4) 0.032(3) Uiso 1 d G
C102 C 1.3896(5) 0.9819(10) 0.9267(4) 0.046(3) Uiso 1 d G
H102 H 1.3883 0.8698 0.9574 0.055 Uiso 1 calc R
C103 C 1.4712(4) 1.0190(12) 0.8963(5) 0.058(4) Uiso 1 d G
H103 H 1.5257 0.9323 0.9062 0.070 Uiso 1 calc R
C104 C 1.4731(5) 1.1831(13) 0.8514(5) 0.052(3) Uiso 1 d G
H104 H 1.5289 1.2085 0.8305 0.062 Uiso 1 calc R
C105 C 1.3934(6) 1.3100(11) 0.8369(4) 0.062(4) Uiso 1 d G
H105 H 1.3946 1.4221 0.8062 0.075 Uiso 1 calc R
C106 C 1.3117(5) 1.2728(11) 0.8674(4) 0.047(3) Uiso 1 d G
H106 H 1.2572 1.3595 0.8575 0.056 Uiso 1 calc R
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'
Br Br -0.6763 1.2805 '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 N21 C1 107.3(8) . .
C9 N22 C6 111.2(8) . .
N21 C1 C10 125.6(8) . 3_777
N21 C1 C2 109.7(8) . .
C10 C1 C2 124.7(9) 3_777 .
C3 C2 C1 106.2(7) . .
C3 C2 Br1 119.8(6) . .
C1 C2 Br1 133.5(7) . .
C2 C3 C4 107.2(7) . .
C2 C3 Br2 120.4(6) . .
C4 C3 Br2 132.0(7) . .
N21 C4 C5 125.9(8) . .
N21 C4 C3 109.5(8) . .
C5 C4 C3 124.6(9) . .
C6 C5 C4 126.0(9) . .
C6 C5 C51 114.7(8) . .
C4 C5 C51 119.0(8) . .
N22 C6 C5 128.1(8) . .
N22 C6 C7 105.9(8) . .
C5 C6 C7 126.0(9) . .
C6 C7 C8 109.4(8) . .
C7 C8 C9 107.1(8) . .
C7 C8 Br3 122.9(9) . .
C9 C8 Br3 130.0(10) . .
C10 C9 N22 128.2(9) . .
C10 C9 C8 125.2(9) . .
N22 C9 C8 106.4(8) . .
C9 C10 C1 125.2(9) . 3_777
C9 C10 C101 115.6(9) . .
C1 C10 C101 119.0(8) 3_777 .
C52 C51 C56 120.0 . .
C52 C51 C5 119.6(5) . .
C56 C51 C5 120.4(5) . .
C51 C52 C53 120.0 . .
C54 C53 C52 120.0 . .
C53 C54 C55 120.0 . .
C54 C55 C56 120.0 . .
C55 C56 C51 120.0 . .
C102 C101 C106 120.0 . .
C102 C101 C10 120.9(6) . .
C106 C101 C10 119.1(6) . .
C103 C102 C101 120.0 . .
C102 C103 C104 120.0 . .
C105 C104 C103 120.0 . .
C106 C105 C104 120.0 . .
C105 C106 C101 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N21 C4 1.356(12) .
N21 C1 1.366(11) .
N22 C9 1.376(11) .
N22 C6 1.377(12) .
C1 C10 1.403(14) 3_777
C1 C2 1.434(10) .
C2 C3 1.368(12) .
C2 Br1 1.895(8) .
C3 C4 1.432(10) .
C3 Br2 1.905(9) .
C4 C5 1.407(12) .
C5 C6 1.394(12) .
C5 C51 1.480(11) .
C6 C7 1.419(10) .
C7 C8 1.380(13) .
C8 C9 1.437(11) .
C8 Br3 1.921(12) .
C9 C10 1.387(13) .
C10 C1 1.403(14) 3_777
C10 C101 1.492(11) .
C51 C52 1.3900 .
C51 C56 1.3900 .
C52 C53 1.3900 .
C53 C54 1.3900 .
C54 C55 1.3900 .
C55 C56 1.3900 .
C101 C102 1.3900 .
C101 C106 1.3900 .
C102 C103 1.3900 .
C103 C104 1.3900 .
C104 C105 1.3900 .
C105 C106 1.3900 .
