#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:10:15 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180171 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/67/7106709.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_7106709
loop_
_publ_author_name
'Joshua Akhigbe'
'John Haskoor'
'Matthias Zeller'
'Christian Bruckner'
_publ_section_title
;
 Porpholactams and chlorolactams: Replacement of a b,b'-double bond in
 meso-tetraphenyl-porphyrin and -chlorin by a lactam moiety
;
_journal_name_full               Chem.Commun.
_journal_page_first              8599
_journal_paper_doi               10.1039/c1cc12955d
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C43 H29 N5 O'
_chemical_formula_weight         631.71
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.720(4)
_cell_angle_beta                 99.884(4)
_cell_angle_gamma                100.532(4)
_cell_formula_units_Z            1
_cell_length_a                   6.3503(15)
_cell_length_b                   10.384(3)
_cell_length_c                   12.353(3)
_cell_measurement_reflns_used    940
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      2.47
_cell_volume                     783.5(3)
_computing_cell_refinement       'Apex2 v2009.7-0'
_computing_data_collection       'Apex2 v2009.7-0 (Bruker, 2009)'
_computing_data_reduction        'Apex2 v2009.7-0'
_computing_molecular_graphics    'SHELXTL 6.14'
_computing_publication_material  'SHELXTL 6.14'
_computing_structure_refinement  'SHELXTL 6.14'
_computing_structure_solution
'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8429
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.01
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 v2009.7-0 (Bruker, 2009)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3844
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0695P)²+0.2590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1591
_reflns_number_gt                2446
_reflns_number_total             3844
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c1cc12955d.txt
_cod_data_source_block           11mz020_0m
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7106709
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.4773(3) 1.0803(2) 0.74422(17) 0.0273(5) Uani 1 1 d . . .
C2 C 0.3550(4) 1.0390(2) 0.82652(18) 0.0337(5) Uani 0.853(2) 1 d PD A 1
H2 H 0.3905 1.0708 0.9031 0.040 Uiso 0.853(2) 1 calc PR A 1
C3 C 0.1786(4) 0.9458(2) 0.77540(18) 0.0320(5) Uani 0.853(2) 1 d PD A 1
H3 H 0.0696 0.9003 0.8101 0.038 Uiso 0.853(2) 1 calc PR A 1
C2C C 0.3550(4) 1.0390(2) 0.82652(18) 0.0337(5) Uani 0.108(2) 1 d PD A 2
N3C N 0.1786(4) 0.9458(2) 0.77540(18) 0.0320(5) Uani 0.108(2) 1 d PD A 2
H3C H 0.0776 0.9036 0.8076 0.038 Uiso 0.108(2) 1 calc PR A 2
O1C O 0.395(2) 1.0469(13) 0.9291(8) 0.0337(5) Uani 0.108(2) 1 d PD A 2
N3D N 0.3550(4) 1.0390(2) 0.82652(18) 0.0337(5) Uani 0.039(3) 1 d PD A 3
H3D H 0.3949 1.0607 0.8985 0.040 Uiso 0.039(3) 1 calc PR A 3
C3D C 0.165(3) 0.960(2) 0.7723(15) 0.0320(5) Uani 0.039(3) 1 d PD A 3
O1D O 0.025(3) 0.934(3) 0.829(3) 0.0320(5) Uani 0.039(3) 1 d PD A 3
C4 C 0.1862(3) 0.92846(19) 0.66061(17) 0.0257(5) Uani 1 1 d D . .
C5 C 0.0429(3) 0.83409(19) 0.58123(17) 0.0254(4) Uani 1 1 d . A .
C6 C 0.0646(3) 0.80970(19) 0.47061(17) 0.0254(4) Uani 1 1 d D . .
C7 C -0.0952(5) 0.7193(3) 0.3907(2) 0.0317(6) Uani 0.647(2) 1 d P A 1
H7 H -0.2283 0.6695 0.4030 0.038 Uiso 0.647(2) 1 calc PR A 1
C8 C -0.0215(3) 0.7178(2) 0.29347(17) 0.0332(5) Uani 0.647(2) 1 d P A 1
H8 H -0.0934 0.6675 0.2251 0.040 Uiso 0.647(2) 1 calc PR A 1
N3A N -0.0952(5) 0.7193(3) 0.3907(2) 0.0317(6) Uani 0.2353(15) 1 d PD A 2
H3A H -0.2185 0.6732 0.4021 0.038 Uiso 0.2353(15) 1 calc PR A 2
C8A C -0.0215(3) 0.7178(2) 0.29347(17) 0.0332(5) Uani 0.2353(15) 1 d PD A 2
O1A O -0.1354(10) 0.6375(6) 0.2183(5) 0.0332(5) Uani 0.2353(15) 1 d PD A 2
C7B C -0.105(3) 0.735(2) 0.3853(14) 0.0317(6) Uani 0.118(2) 1 d PD A 3
N3B N -0.0215(3) 0.7178(2) 0.29347(17) 0.0332(5) Uani 0.118(2) 1 d PD A 3
H3B H -0.0813 0.6632 0.2333 0.040 Uiso 0.118(2) 1 calc PR A 3
O1B O -0.2998(17) 0.6884(12) 0.3720(10) 0.0317(6) Uani 0.118(2) 1 d PD A 3
C9 C 0.1878(3) 0.8077(2) 0.31459(17) 0.0270(5) Uani 1 1 d D . .
C10 C 0.3207(3) 0.8317(2) 0.23586(16) 0.0268(5) Uani 1 1 d . . .
C11 C -0.1394(3) 0.7471(2) 0.61847(16) 0.0260(5) Uani 1 1 d . . .
C12 C -0.1524(3) 0.6111(2) 0.61007(18) 0.0300(5) Uani 1 1 d . A .
H12 H -0.0459 0.5740 0.5800 0.036 Uiso 1 1 calc R . .
C13 C -0.3194(4) 0.5296(2) 0.64523(19) 0.0351(5) Uani 1 1 d . . .
H13 H -0.3287 0.4368 0.6376 0.042 Uiso 1 1 calc R A .
C14 C -0.4721(4) 0.5827(2) 0.69118(18) 0.0328(5) Uani 1 1 d . A .
H14 H -0.5849 0.5268 0.7165 0.039 Uiso 1 1 calc R . .
C15 C -0.4608(4) 0.7175(2) 0.70036(19) 0.0343(5) Uani 1 1 d . . .
H15 H -0.5660 0.7542 0.7320 0.041 Uiso 1 1 calc R A .
C16 C -0.2960(3) 0.7994(2) 0.66353(18) 0.0308(5) Uani 1 1 d . A .
H16 H -0.2903 0.8918 0.6692 0.037 Uiso 1 1 calc R . .
C17 C 0.2418(3) 0.7614(2) 0.12116(17) 0.0308(5) Uani 1 1 d . . .
C18 C 0.0485(4) 0.7785(2) 0.05643(19) 0.0388(6) Uani 1 1 d . A .
H18 H -0.0337 0.8369 0.0843 0.047 Uiso 1 1 calc R . .
C19 C -0.0239(4) 0.7100(3) -0.0490(2) 0.0492(7) Uani 1 1 d . . .
H19 H -0.1570 0.7206 -0.0924 0.059 Uiso 1 1 calc R A .
C20 C 0.0961(5) 0.6270(3) -0.0907(2) 0.0519(7) Uani 1 1 d . A .
H20 H 0.0460 0.5806 -0.1628 0.062 Uiso 1 1 calc R . .
C21 C 0.2875(5) 0.6113(2) -0.0285(2) 0.0488(7) Uani 1 1 d . . .
H21 H 0.3710 0.5548 -0.0579 0.059 Uiso 1 1 calc R A .
C22 C 0.3605(4) 0.6773(2) 0.07734(19) 0.0399(6) Uani 1 1 d . A .
H22 H 0.4929 0.6648 0.1202 0.048 Uiso 1 1 calc R . .
N1 N 0.3685(3) 1.01228(16) 0.64412(14) 0.0259(4) Uani 1 1 d . A .
H1 H 0.4090 1.0211 0.5801 0.031 Uiso 0.5690(16) 1 calc PR . .
N2 N 0.2335(3) 0.86252(16) 0.42285(13) 0.0250(4) Uani 1 1 d . A .
H2A H 0.3503 0.9210 0.4555 0.030 Uiso 0.4310(16) 1 calc PR . .
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'
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
N1 C1 C10 126.48(19) . 2_676 ?
N1 C1 C2 107.81(18) . . ?
C10 C1 C2 125.59(19) 2_676 . ?
C3 C2 C1 107.59(19) . . ?
C3 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
C2 C3 C4 108.0(2) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
O1D C3D C4 137(2) . . ?
N1 C4 C5 126.34(19) . . ?
N1 C4 C3 107.89(18) . . ?
C5 C4 C3 125.5(2) . . ?
N1 C4 C3D 107.0(8) . . ?
C5 C4 C3D 126.6(8) . . ?
C4 C5 C6 124.92(19) . . ?
C4 C5 C11 117.64(18) . . ?
C6 C5 C11 117.34(17) . . ?
N2 C6 C5 127.56(18) . . ?
N2 C6 C7 109.72(19) . . ?
C5 C6 C7 122.7(2) . . ?
N2 C6 C7B 108.1(7) . . ?
C5 C6 C7B 123.9(7) . . ?
C8 C7 C6 107.3(2) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 106.6(2) . . ?
C7 C8 H8 126.7 . . ?
C9 C8 H8 126.7 . . ?
O1B C7B C6 138.5(15) . . ?
N2 C9 C10 126.47(18) . . ?
N2 C9 C8 108.99(18) . . ?
C10 C9 C8 124.53(18) . . ?
C1 C10 C9 124.68(19) 2_676 . ?
C1 C10 C17 116.85(19) 2_676 . ?
C9 C10 C17 118.46(18) . . ?
C16 C11 C12 118.73(19) . . ?
C16 C11 C5 121.23(18) . . ?
C12 C11 C5 120.03(19) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C22 C17 C18 118.7(2) . . ?
C22 C17 C10 120.3(2) . . ?
C18 C17 C10 121.0(2) . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
C4 N1 C1 108.73(17) . . ?
C4 N1 H1 125.6 . . ?
C1 N1 H1 125.6 . . ?
C6 N2 C9 107.33(16) . . ?
C6 N2 H2A 126.3 . . ?
C9 N2 H2A 126.3 . . ?
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
C1 N1 1.375(3) . ?
C1 C10 1.403(3) 2_676 ?
C1 C2 1.429(3) . ?
C2 C3 1.361(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.425(3) . ?
C3 H3 0.9500 . ?
C3D O1D 1.229(17) . ?
C3D C4 1.425(18) . ?
C4 N1 1.371(3) . ?
C4 C5 1.400(3) . ?
C5 C6 1.404(3) . ?
C5 C11 1.496(3) . ?
C6 N2 1.362(3) . ?
C6 C7 1.428(4) . ?
C6 C7B 1.430(16) . ?
C7 C8 1.362(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.446(3) . ?
C8 H8 0.9500 . ?
C7B O1B 1.219(15) . ?
C9 N2 1.370(3) . ?
C9 C10 1.402(3) . ?
C10 C1 1.403(3) 2_676 ?
C10 C17 1.498(3) . ?
C11 C16 1.390(3) . ?
C11 C12 1.393(3) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.388(3) . ?
C17 C18 1.394(3) . ?
C18 C19 1.392(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.366(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
N1 H1 0.8800 . ?
N2 H2A 0.8800 . ?
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
N1 C1 C2 C3 1.2(3) . . . . ?
C10 C1 C2 C3 -175.1(2) 2_676 . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 N1 -0.1(3) . . . . ?
C2 C3 C4 C5 174.8(2) . . . . ?
C2 C3 C4 C3D -84(6) . . . . ?
O1D C3D C4 N1 167(3) . . . . ?
O1D C3D C4 C5 -10(3) . . . . ?
O1D C3D C4 C3 -95(7) . . . . ?
N1 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 C6 -173.6(2) . . . . ?
C3D C4 C5 C6 177.4(14) . . . . ?
N1 C4 C5 C11 176.47(18) . . . . ?
C3 C4 C5 C11 2.5(3) . . . . ?
C3D C4 C5 C11 -6.5(14) . . . . ?
C4 C5 C6 N2 6.3(3) . . . . ?
C11 C5 C6 N2 -169.82(19) . . . . ?
C4 C5 C6 C7 -175.0(2) . . . . ?
C11 C5 C6 C7 8.8(3) . . . . ?
C4 C5 C6 C7B -165.5(11) . . . . ?
C11 C5 C6 C7B 18.4(11) . . . . ?
N2 C6 C7 C8 0.0(3) . . . . ?
C5 C6 C7 C8 -178.9(2) . . . . ?
C7B C6 C7 C8 80(5) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
N2 C6 C7B O1B -163(2) . . . . ?
C5 C6 C7B O1B 10(3) . . . . ?
C7 C6 C7B O1B 94(6) . . . . ?
C7 C8 C9 N2 -0.9(3) . . . . ?
C7 C8 C9 C10 178.3(2) . . . . ?
N2 C9 C10 C1 -1.5(3) . . . 2_676 ?
C8 C9 C10 C1 179.4(2) . . . 2_676 ?
N2 C9 C10 C17 179.77(19) . . . . ?
C8 C9 C10 C17 0.7(3) . . . . ?
C4 C5 C11 C16 60.7(3) . . . . ?
C6 C5 C11 C16 -122.8(2) . . . . ?
C4 C5 C11 C12 -118.2(2) . . . . ?
C6 C5 C11 C12 58.3(3) . . . . ?
C16 C11 C12 C13 0.5(3) . . . . ?
C5 C11 C12 C13 179.4(2) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C11 -0.8(3) . . . . ?
C12 C11 C16 C15 0.6(3) . . . . ?
C5 C11 C16 C15 -178.29(19) . . . . ?
C1 C10 C17 C22 61.9(3) 2_676 . . . ?
C9 C10 C17 C22 -119.3(2) . . . . ?
C1 C10 C17 C18 -118.2(2) 2_676 . . . ?
C9 C10 C17 C18 60.6(3) . . . . ?
C22 C17 C18 C19 1.2(3) . . . . ?
C10 C17 C18 C19 -178.6(2) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C22 0.8(4) . . . . ?
C20 C21 C22 C17 -0.7(4) . . . . ?
C18 C17 C22 C21 -0.3(3) . . . . ?
C10 C17 C22 C21 179.6(2) . . . . ?
C5 C4 N1 C1 -174.01(19) . . . . ?
C3 C4 N1 C1 0.8(2) . . . . ?
C3D C4 N1 C1 8.5(12) . . . . ?
C10 C1 N1 C4 175.0(2) 2_676 . . . ?
C2 C1 N1 C4 -1.2(2) . . . . ?
C5 C6 N2 C9 178.24(19) . . . . ?
C7 C6 N2 C9 -0.6(2) . . . . ?
C7B C6 N2 C9 -8.9(10) . . . . ?
C10 C9 N2 C6 -178.3(2) . . . . ?
C8 C9 N2 C6 0.9(2) . . . . ?
