data_he006
_audit_creation_date               2020-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/1'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          5,15-dibromo-10,20-di-p-tolylporphyrin
_chemical_formula_moiety           'C34 H24 Br2 N4'
_chemical_formula_sum              'C34 H24 Br2 N4'
_chemical_formula_weight           648.39
_chemical_melting_point            ?
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'
 'Br' 'Br' -0.6763 1.2805
 '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'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             60
_space_group_name_H-M_alt          'P b c n'
_space_group_name_Hall             '-P 2n 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y+1/2, z+1/2'
 '-x, y, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y-1/2, -z-1/2'
 'x, -y, z-1/2'
 '-x-1/2, y-1/2, z'

_cell_length_a                     16.6909(12)
_cell_length_b                     6.2095(4)
_cell_length_c                     25.1966(17)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       2611.4(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      7947
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        66.96
_cell_measurement_theta_min        3.51
_shelx_estimated_absorpt_T_max     0.366
_shelx_estimated_absorpt_T_min     0.285
_exptl_absorpt_coefficient_mu      4.191
_exptl_absorpt_correction_T_max    0.7529
_exptl_absorpt_correction_T_min    0.5897
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0792 before and 0.0432 after correction. The Ratio of minimum to maximum transmission is 0.7832. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              red
_exptl_crystal_colour_primary      red
_exptl_crystal_density_diffrn      1.649
_exptl_crystal_density_meas        .
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         parallelepiped
_exptl_crystal_F_000               1304
_exptl_crystal_preparation         ?
_exptl_crystal_size_max            0.4
_exptl_crystal_size_mid            0.35
_exptl_crystal_size_min            0.3
_exptl_special_details
;
 ? 
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0295
_diffrn_reflns_av_unetI/netI       0.0262
_diffrn_reflns_Laue_measured_fraction_full  0.970
_diffrn_reflns_Laue_measured_fraction_max  0.970
_diffrn_reflns_limit_h_max         19
_diffrn_reflns_limit_h_min         -19
_diffrn_reflns_limit_k_max         4
_diffrn_reflns_limit_k_min         -7
_diffrn_reflns_limit_l_max         30
_diffrn_reflns_limit_l_min         -29
_diffrn_reflns_number              12171
_diffrn_reflns_point_group_measured_fraction_full  0.970
_diffrn_reflns_point_group_measured_fraction_max  0.970
_diffrn_reflns_theta_full          67.098
_diffrn_reflns_theta_max           67.098
_diffrn_reflns_theta_min           3.508
_diffrn_ambient_temperature        99.99
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.970
_diffrn_measured_fraction_theta_max  0.970
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2141
_reflns_number_total               2265
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max           0.542
_refine_diff_density_min           -0.319
_refine_diff_density_rms           0.070
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.058
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       182
_refine_ls_number_reflns           2265
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0295
_refine_ls_R_factor_gt             0.0282
_refine_ls_restrained_S_all        1.058
_refine_ls_shift/su_max            0.002
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0438P)²+2.4696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0757
_refine_ls_wR_factor_ref           0.0772
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N21(H21), C2(H2), C3(H3), C7(H7), C8(H8), C102(H102), C103(H103), C105(H105),
 C106(H106)
2.b Idealised Me refined as rotating group:
 C107(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       ?
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 N21 N -0.07913(10) 0.6737(3) 0.54712(6) 0.0158(3) Uani 1 1 d . . . . .
 H21 H -0.042776 0.605165 0.528297 0.019 Uiso 1 1 calc R . . . .
 N22 N -0.01334(10) 0.7184(3) 0.43953(7) 0.0162(4) Uani 1 1 d . . . . .
 C1 C -0.10386(11) 0.6180(3) 0.59716(7) 0.0164(4) Uani 1 1 d . . . . .
 C2 C -0.16498(12) 0.7675(4) 0.61257(8) 0.0182(4) Uani 1 1 d . . . . .
 H2 H -0.193686 0.766063 0.645125 0.022 Uiso 1 1 calc R . . . .
 C3 C -0.17472(11) 0.9115(4) 0.57264(8) 0.0188(4) Uani 1 1 d . . . . .
 H3 H -0.211076 1.029219 0.572272 0.023 Uiso 1 1 calc R . . . .
 C4 C -0.12027(12) 0.8538(4) 0.53114(7) 0.0172(4) Uani 1 1 d . . . . .
 C5 C -0.11052(11) 0.9559(3) 0.48246(8) 0.0174(4) Uani 1 1 d . . . . .
 C6 C -0.06147(11) 0.8974(3) 0.43991(8) 0.0171(4) Uani 1 1 d . . . . .
 C7 C -0.05683(12) 1.0085(3) 0.38966(8) 0.0196(4) Uani 1 1 d . . . . .
 H7 H -0.083106 1.138873 0.380341 0.024 Uiso 1 1 calc R . . . .
 C8 C -0.00777(12) 0.8906(3) 0.35860(8) 0.0198(4) Uani 1 1 d . . . . .
 H8 H 0.005604 0.919857 0.322663 0.024 Uiso 1 1 calc R . . . .
 C9 C 0.02078(12) 0.7112(3) 0.39010(8) 0.0168(4) Uani 1 1 d . . . . .
 C10 C 0.07530(11) 0.5545(3) 0.37234(7) 0.0170(4) Uani 1 1 d . . . . .
 Br1 Br -0.17408(2) 1.20922(4) 0.47290(2) 0.02375(12) Uani 1 1 d . . . . .
 C101 C 0.10477(11) 0.5669(3) 0.31629(7) 0.0174(4) Uani 1 1 d . . . . .
 C102 C 0.14476(13) 0.7475(4) 0.29667(8) 0.0204(4) Uani 1 1 d . . . . .
 H102 H 0.154756 0.866377 0.319450 0.024 Uiso 1 1 calc R . . . .
 C103 C 0.17008(12) 0.7552(4) 0.24425(9) 0.0216(5) Uani 1 1 d . . . . .
 H103 H 0.196819 0.880237 0.231647 0.026 Uiso 1 1 calc R . . . .
 C104 C 0.15712(12) 0.5838(4) 0.20981(8) 0.0207(4) Uani 1 1 d . . . . .
 C105 C 0.11808(12) 0.4035(4) 0.22948(8) 0.0227(5) Uani 1 1 d . . . . .
 H105 H 0.108973 0.283929 0.206734 0.027 Uiso 1 1 calc R . . . .
 C106 C 0.09207(12) 0.3942(3) 0.28174(8) 0.0206(4) Uani 1 1 d . . . . .
 H106 H 0.065309 0.269011 0.294174 0.025 Uiso 1 1 calc R . . . .
 C107 C 0.18638(14) 0.5917(4) 0.15319(8) 0.0265(5) Uani 1 1 d . . . . .
 H10A H 0.244114 0.563208 0.152324 0.040 Uiso 1 1 calc GR . . . .
 H10B H 0.175743 0.734666 0.138276 0.040 Uiso 1 1 calc GR . . . .
 H10C H 0.158290 0.482460 0.132178 0.040 Uiso 1 1 calc GR . . . .


_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
 N21 H21 0.8800 . ?
 N21 C1 1.371(2) . ?
 N21 C4 1.373(3) . ?
 N22 C6 1.371(3) . ?
 N22 C9 1.370(3) . ?
 C1 C2 1.433(3) . ?
 C1 C10 1.402(3) 5_566 ?
 C2 H2 0.9500 . ?
 C2 C3 1.356(3) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.431(3) . ?
 C4 C5 1.390(3) . ?
 C5 C6 1.397(3) . ?
 C5 Br1 1.913(2) . ?
 C6 C7 1.444(3) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.349(3) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.448(3) . ?
 C9 C10 1.406(3) . ?
 C10 C101 1.497(3) . ?
 C101 C102 1.396(3) . ?
 C101 C106 1.397(3) . ?
 C102 H102 0.9500 . ?
 C102 C103 1.387(3) . ?
 C103 H103 0.9500 . ?
 C103 C104 1.390(3) . ?
 C104 C105 1.387(3) . ?
 C104 C107 1.509(3) . ?
 C105 H105 0.9500 . ?
 C105 C106 1.388(3) . ?
 C106 H106 0.9500 . ?
 C107 H10A 0.9800 . ?
 C107 H10B 0.9800 . ?
 C107 H10C 0.9800 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C1 N21 H21 125.5 . . ?
 C1 N21 C4 108.96(16) . . ?
 C4 N21 H21 125.5 . . ?
 C9 N22 C6 106.03(16) . . ?
 N21 C1 C2 107.44(18) . . ?
 N21 C1 C10 126.50(18) . 5_566 ?
 C10 C1 C2 126.06(18) 5_566 . ?
 C1 C2 H2 125.9 . . ?
 C3 C2 C1 108.16(18) . . ?
 C3 C2 H2 125.9 . . ?
 C2 C3 H3 126.2 . . ?
 C2 C3 C4 107.52(19) . . ?
 C4 C3 H3 126.2 . . ?
 N21 C4 C3 107.90(17) . . ?
 N21 C4 C5 124.87(18) . . ?
 C5 C4 C3 127.2(2) . . ?
 C4 C5 C6 128.84(19) . . ?
 C4 C5 Br1 114.91(15) . . ?
 C6 C5 Br1 116.25(15) . . ?
 N22 C6 C5 124.01(18) . . ?
 N22 C6 C7 110.48(17) . . ?
 C5 C6 C7 125.45(19) . . ?
 C6 C7 H7 126.8 . . ?
 C8 C7 C6 106.37(18) . . ?
 C8 C7 H7 126.8 . . ?
 C7 C8 H8 126.3 . . ?
 C7 C8 C9 107.41(18) . . ?
 C9 C8 H8 126.3 . . ?
 N22 C9 C8 109.66(18) . . ?
 N22 C9 C10 125.52(18) . . ?
 C10 C9 C8 124.82(19) . . ?
 C1 C10 C9 125.08(18) 5_566 . ?
 C1 C10 C101 116.39(18) 5_566 . ?
 C9 C10 C101 118.52(18) . . ?
 C102 C101 C10 122.16(18) . . ?
 C102 C101 C106 117.92(18) . . ?
 C106 C101 C10 119.91(18) . . ?
 C101 C102 H102 119.6 . . ?
 C103 C102 C101 120.7(2) . . ?
 C103 C102 H102 119.6 . . ?
 C102 C103 H103 119.3 . . ?
 C102 C103 C104 121.3(2) . . ?
 C104 C103 H103 119.3 . . ?
 C103 C104 C107 121.0(2) . . ?
 C105 C104 C103 117.90(19) . . ?
 C105 C104 C107 121.1(2) . . ?
 C104 C105 H105 119.4 . . ?
 C104 C105 C106 121.3(2) . . ?
 C106 C105 H105 119.4 . . ?
 C101 C106 H106 119.6 . . ?
 C105 C106 C101 120.8(2) . . ?
 C105 C106 H106 119.6 . . ?
 C104 C107 H10A 109.5 . . ?
 C104 C107 H10B 109.5 . . ?
 C104 C107 H10C 109.5 . . ?
 H10A C107 H10B 109.5 . . ?
 H10A C107 H10C 109.5 . . ?
 H10B C107 H10C 109.5 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 N21 C1 C2 C3 -1.3(2) . . . . ?
 N21 C4 C5 C6 2.6(3) . . . . ?
 N21 C4 C5 Br1 -178.00(16) . . . . ?
 N22 C6 C7 C8 2.1(2) . . . . ?
 N22 C9 C10 C1 -0.7(3) . . . 5_566 ?
 N22 C9 C10 C101 178.00(18) . . . . ?
 C1 N21 C4 C3 -1.3(2) . . . . ?
 C1 N21 C4 C5 179.92(19) . . . . ?
 C1 C2 C3 C4 0.5(2) . . . . ?
 C1 C10 C101 C102 -122.6(2) 5_566 . . . ?
 C1 C10 C101 C106 57.7(3) 5_566 . . . ?
 C2 C3 C4 N21 0.5(2) . . . . ?
 C2 C3 C4 C5 179.2(2) . . . . ?
 C3 C4 C5 C6 -176.0(2) . . . . ?
 C3 C4 C5 Br1 3.4(3) . . . . ?
 C4 N21 C1 C2 1.6(2) . . . . ?
 C4 N21 C1 C10 -178.91(19) . . . 5_566 ?
 C4 C5 C6 N22 0.8(3) . . . . ?
 C4 C5 C6 C7 177.7(2) . . . . ?
 C5 C6 C7 C8 -175.16(19) . . . . ?
 C6 N22 C9 C8 -0.6(2) . . . . ?
 C6 N22 C9 C10 179.36(19) . . . . ?
 C6 C7 C8 C9 -2.4(2) . . . . ?
 C7 C8 C9 N22 1.9(2) . . . . ?
 C7 C8 C9 C10 -178.01(19) . . . . ?
 C8 C9 C10 C1 179.21(19) . . . 5_566 ?
 C8 C9 C10 C101 -2.1(3) . . . . ?
 C9 N22 C6 C5 176.41(18) . . . . ?
 C9 N22 C6 C7 -0.9(2) . . . . ?
 C9 C10 C101 C102 58.5(3) . . . . ?
 C9 C10 C101 C106 -121.1(2) . . . . ?
 C10 C1 C2 C3 179.21(19) 5_566 . . . ?
 C10 C101 C102 C103 -178.88(19) . . . . ?
 C10 C101 C106 C105 179.25(19) . . . . ?
 Br1 C5 C6 N22 -178.61(15) . . . . ?
 Br1 C5 C6 C7 -1.7(3) . . . . ?
 C101 C102 C103 C104 -0.5(3) . . . . ?
 C102 C101 C106 C105 -0.4(3) . . . . ?
 C102 C103 C104 C105 -0.2(3) . . . . ?
 C102 C103 C104 C107 -178.7(2) . . . . ?
 C103 C104 C105 C106 0.5(3) . . . . ?
 C104 C105 C106 C101 -0.2(3) . . . . ?
 C106 C101 C102 C103 0.8(3) . . . . ?
 C107 C104 C105 C106 179.1(2) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
_vrf_PLAT029_he006
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.970 Why?  
RESPONSE: This is due to weak high angle data.
;
_vrf_PLAT911_he006
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.597         70 Report
RESPONSE: The structure was collected to 97% completeness resulting in 
the missing reflections.
;
