#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:19:50 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180034 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/28/7032821.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_7032821
loop_
_publ_author_name
'Işci, Umit'
'Caner, Celal'
'Zorlu, Yunus'
'Gürek, Ayşe Gül'
'Dumoulin, Fabienne'
'Ahsen, Vefa'
_publ_section_title
;
 Sulfonamide-substituted iron phthalocyanine: design, solubility range,
 stability and oxidation of olefins.
;
_journal_issue                   48
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17916
_journal_page_last               17919
_journal_paper_doi               10.1039/c4dt02412e
_journal_volume                  43
_journal_year                    2014
_chemical_formula_moiety         ' C18 H17 N3 O2 S '
_chemical_formula_sum            'C18 H17 N3 O2 S'
_chemical_formula_weight         339.41
_chemical_name_common            phthalonitrile
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5105(6)
_cell_length_b                   8.8219(6)
_cell_length_c                   21.8277(14)
_cell_measurement_reflns_used    114
_cell_measurement_temperature    130.(2)
_cell_measurement_theta_max      26.6224
_cell_measurement_theta_min      4.3525
_cell_volume                     1638.80(19)
_computing_cell_refinement       'APEX2 v2012.10-0 (Bruker AXS)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS, 2009)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11431
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.288
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2837
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0401P)²+0.3418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0742
_reflns_number_gt                2713
_reflns_number_total             2837
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4dt02412e2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7032821.cif.'
_cod_database_code               7032821
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.8592(2) -0.2035(2) 0.45272(10) 0.0209(5) Uani d . 1
C C2 1.0132(2) -0.4528(2) 0.38858(9) 0.0201(4) Uani d . 1
C C3 1.0485(2) -0.2972(2) 0.37481(10) 0.0176(4) Uani d . 1
C C4 1.1548(3) -0.2650(2) 0.32810(10) 0.0206(5) Uani d . 1
H H4 1.2051 -0.346 0.3072 0.025 Uiso calc R 1
C C5 1.1884(2) -0.1167(2) 0.31165(9) 0.0188(4) Uani d . 1
H H5 1.2608 -0.0965 0.2796 0.023 Uiso calc R 1
C C6 1.1154(2) 0.0027(2) 0.34233(9) 0.0160(4) Uani d . 1
C C7 1.0093(2) -0.0276(2) 0.38959(9) 0.0170(4) Uani d . 1
H H7 0.9605 0.0537 0.4109 0.02 Uiso calc R 1
C C8 0.9751(2) -0.1762(2) 0.40543(9) 0.0176(4) Uani d . 1
C C9 1.0696(2) 0.2443(2) 0.21368(9) 0.0165(4) Uani d . 1
C C10 0.9566(2) 0.3572(2) 0.22065(9) 0.0184(4) Uani d . 1
H H10 0.9622 0.4265 0.2539 0.022 Uiso calc R 1
C C11 0.8364(2) 0.3664(2) 0.17847(9) 0.0193(4) Uani d . 1
H H11 0.759 0.4432 0.1833 0.023 Uiso calc R 1
C C12 0.8244(2) 0.2672(2) 0.12908(10) 0.0179(4) Uani d . 1
C C13 0.9396(2) 0.1567(3) 0.12314(10) 0.0242(5) Uani d . 1
H H13 0.9346 0.088 0.0897 0.029 Uiso calc R 1
C C14 1.0623(2) 0.1440(3) 0.16501(10) 0.0234(5) Uani d . 1
H H14 1.14 0.0676 0.1602 0.028 Uiso calc R 1
C C15 0.6877(3) 0.2851(2) 0.08379(10) 0.0220(5) Uani d . 1
C C16 0.5315(3) 0.2747(3) 0.11891(11) 0.0260(5) Uani d . 1
H H16A 0.4438 0.2791 0.0899 0.039 Uiso calc R 1
H H16B 0.5237 0.3596 0.1477 0.039 Uiso calc R 1
H H16C 0.5275 0.1788 0.1415 0.039 Uiso calc R 1
C C17 0.6883(3) 0.1644(3) 0.03402(11) 0.0317(5) Uani d . 1
H H17A 0.7863 0.1712 0.0106 0.048 Uiso calc R 1
H H17B 0.5987 0.1803 0.0066 0.048 Uiso calc R 1
H H17C 0.6804 0.0639 0.0529 0.048 Uiso calc R 1
C C18 0.6977(3) 0.4423(3) 0.05371(12) 0.0380(6) Uani d . 1
H H18A 0.7965 0.4507 0.0309 0.057 Uiso calc R 1
H H18B 0.6941 0.5207 0.0855 0.057 Uiso calc R 1
H H18C 0.609 0.4557 0.0256 0.057 Uiso calc R 1
H H1N 1.090(3) 0.226(3) 0.3510(12) 0.046 Uiso d D 1
N N1 0.7642(3) -0.2202(2) 0.48896(11) 0.0341(5) Uani d . 1
N N2 0.9886(2) -0.5786(2) 0.39683(8) 0.0261(4) Uani d . 1
N N3 1.1454(2) 0.15609(19) 0.33014(7) 0.0177(4) Uani d D 1
O O1 1.26024(16) 0.38223(15) 0.28665(7) 0.0213(3) Uani d . 1
O O2 1.34011(15) 0.13238(15) 0.24522(7) 0.0215(3) Uani d . 1
S S1 1.22195(5) 0.23207(5) 0.26784(2) 0.01635(12) Uani d . 1
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'
S S 0.1246 0.1234 '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
N1 C1 C8 177.2(2)
N2 C2 C3 176.6(2)
C4 C3 C8 118.80(18)
C4 C3 C2 118.96(19)
C8 C3 C2 122.19(19)
C5 C4 C3 121.09(19)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 C6 119.79(19)
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 C7 119.87(19)
C5 C6 N3 123.86(18)
C7 C6 N3 116.24(17)
C8 C7 C6 120.04(18)
C8 C7 H7 120.0
C6 C7 H7 120.0
C7 C8 C3 120.41(18)
C7 C8 C1 118.51(19)
C3 C8 C1 121.05(19)
C14 C9 C10 120.67(19)
C14 C9 S1 120.65(16)
C10 C9 S1 118.68(15)
C11 C10 C9 118.80(19)
C11 C10 H10 120.6
C9 C10 H10 120.6
C10 C11 C12 122.28(19)
C10 C11 H11 118.9
C12 C11 H11 118.9
C13 C12 C11 117.53(19)
C13 C12 C15 123.2(2)
C11 C12 C15 119.30(18)
C12 C13 C14 121.6(2)
C12 C13 H13 119.2
C14 C13 H13 119.2
C9 C14 C13 119.1(2)
C9 C14 H14 120.5
C13 C14 H14 120.5
C17 C15 C12 112.65(18)
C17 C15 C16 108.53(18)
C12 C15 C16 109.16(18)
C17 C15 C18 109.04(19)
C12 C15 C18 109.00(17)
C16 C15 C18 108.37(19)
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C15 C17 H17A 109.5
C15 C17 H17B 109.5
H17A C17 H17B 109.5
C15 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C6 N3 S1 128.31(14)
C6 N3 H1N 118.1(19)
S1 N3 H1N 110.2(19)
O2 S1 O1 120.84(8)
O2 S1 N3 108.28(9)
O1 S1 N3 103.33(9)
O2 S1 C9 109.00(9)
O1 S1 C9 107.78(9)
N3 S1 C9 106.73(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.141(3)
C1 C8 1.448(3)
C2 N2 1.143(3)
C2 C3 1.437(3)
C3 C4 1.392(3)
C3 C8 1.406(3)
C4 C5 1.387(3)
C4 H4 0.95
C5 C6 1.394(3)
C5 H5 0.95
C6 C7 1.397(3)
C6 N3 1.402(3)
C7 C8 1.387(3)
C7 H7 0.95
C9 C14 1.384(3)
C9 C10 1.393(3)
C9 S1 1.7581(19)
C10 C11 1.378(3)
C10 H10 0.95
C11 C12 1.392(3)
C11 H11 0.95
C12 C13 1.389(3)
C12 C15 1.535(3)
C13 C14 1.392(3)
C13 H13 0.95
C14 H14 0.95
C15 C17 1.521(3)
C15 C16 1.537(3)
C15 C18 1.537(3)
C16 H16A 0.98
C16 H16B 0.98
C16 H16C 0.98
C17 H17A 0.98
C17 H17B 0.98
C17 H17C 0.98
C18 H18A 0.98
C18 H18B 0.98
C18 H18C 0.98
N3 S1 1.6503(17)
N3 H1N 0.898(17)
O1 S1 1.4246(14)
O2 S1 1.4242(14)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H1N N2 1_565 0.898(17) 2.174(18) 3.062(3) 170.(3)
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
N2 C2 C3 C4 -14.(4)
N2 C2 C3 C8 164.(4)
C8 C3 C4 C5 -0.1(3)
C2 C3 C4 C5 177.67(19)
C3 C4 C5 C6 0.2(3)
C4 C5 C6 C7 0.2(3)
C4 C5 C6 N3 178.06(18)
C5 C6 C7 C8 -0.8(3)
N3 C6 C7 C8 -178.81(17)
C6 C7 C8 C3 1.0(3)
C6 C7 C8 C1 -177.21(18)
C4 C3 C8 C7 -0.5(3)
C2 C3 C8 C7 -178.18(19)
C4 C3 C8 C1 177.59(19)
C2 C3 C8 C1 -0.1(3)
N1 C1 C8 C7 41.(5)
N1 C1 C8 C3 -138.(5)
C14 C9 C10 C11 0.6(3)
S1 C9 C10 C11 -179.59(15)
C9 C10 C11 C12 -0.2(3)
C10 C11 C12 C13 -0.3(3)
C10 C11 C12 C15 -179.70(19)
C11 C12 C13 C14 0.4(3)
C15 C12 C13 C14 179.8(2)
C10 C9 C14 C13 -0.4(3)
S1 C9 C14 C13 179.74(16)
C12 C13 C14 C9 -0.1(3)
C13 C12 C15 C17 2.8(3)
C11 C12 C15 C17 -177.83(19)
C13 C12 C15 C16 123.4(2)
C11 C12 C15 C16 -57.2(2)
C13 C12 C15 C18 -118.4(2)
C11 C12 C15 C18 61.0(3)
C5 C6 N3 S1 20.5(3)
C7 C6 N3 S1 -161.52(15)
C6 N3 S1 O2 -36.84(19)
C6 N3 S1 O1 -166.11(16)
C6 N3 S1 C9 80.37(18)
C14 C9 S1 O2 12.08(19)
C10 C9 S1 O2 -167.77(15)
C14 C9 S1 O1 144.91(17)
C10 C9 S1 O1 -34.94(18)
C14 C9 S1 N3 -104.66(18)
C10 C9 S1 N3 75.50(17)
