#------------------------------------------------------------------------------
#$Date: 2018-09-11 14:27:57 +0200 (mar 11 de sep de 2018) $
#$Revision: 210836 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/40/7104045.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_7104045
loop_
_publ_author_name
'Nath, Mahendra'
'Huffman, John C.'
'Zaleski, Jeffrey M.'
_publ_section_title
;
 Accelerated Bergman cyclization of porphyrinic-enediynes
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   7
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              858
_journal_page_last               859
_journal_paper_doi               10.1039/b212923j
_journal_year                    2003
_chemical_formula_sum            'C48 H30 N4'
_chemical_formula_weight         662.76
_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                 97.5350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4177(5)
_cell_length_b                   10.0068(4)
_cell_length_c                   23.8356(9)
_cell_measurement_reflns_used    7809
_cell_measurement_temperature    114(2)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      2.2
_cell_volume                     3409.2(2)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999), XTEL (local package)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      114(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 44.52
_diffrn_detector_type            'Bruker SMART 6000'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker Platform goniometer'
_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  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            46218
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        0.0016
_diffrn_standards_number         328
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     589
_refine_ls_number_reflns         9941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0500
_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)+(0.0779P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1356
_reflns_number_gt                6558
_reflns_number_total             9941
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b212923j.txt
_cod_data_source_block           02084
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7104045
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.50740(8) 0.92017(11) 0.10520(5) 0.0229(2) Uani 1 1 d . . .
C2 C 0.44370(9) 0.86360(13) 0.06458(6) 0.0218(3) Uani 1 1 d . . .
C3 C 0.34855(9) 0.88662(14) 0.07736(6) 0.0232(3) Uani 1 1 d . . .
C4 C 0.35680(9) 0.96476(14) 0.12509(6) 0.0233(3) Uani 1 1 d . . .
C5 C 0.45730(9) 0.98106(14) 0.14285(6) 0.0225(3) Uani 1 1 d . . .
C6 C 0.49584(9) 1.04657(14) 0.19288(6) 0.0236(3) Uani 1 1 d . . .
C7 C 0.59112(9) 1.05437(14) 0.21370(6) 0.0244(3) Uani 1 1 d . . .
C8 C 0.63006(10) 1.12484(15) 0.26347(6) 0.0286(3) Uani 1 1 d . . .
C9 C 0.72509(10) 1.11263(15) 0.26898(6) 0.0278(3) Uani 1 1 d . . .
C10 C 0.74805(9) 1.03192(14) 0.22285(6) 0.0238(3) Uani 1 1 d . . .
N11 N 0.66507(8) 0.99898(12) 0.19068(5) 0.0242(2) Uani 1 1 d . . .
C12 C 0.83799(9) 0.99759(14) 0.21138(6) 0.0233(3) Uani 1 1 d . . .
C13 C 0.85781(9) 0.93132(14) 0.16212(6) 0.0229(3) Uani 1 1 d . . .
C14 C 0.95179(9) 0.89207(15) 0.15227(6) 0.0259(3) Uani 1 1 d . . .
C15 C 0.94357(10) 0.83812(15) 0.10017(6) 0.0266(3) Uani 1 1 d . . .
C16 C 0.84431(9) 0.84322(14) 0.07775(6) 0.0239(3) Uani 1 1 d . . .
N17 N 0.79338(8) 0.89775(12) 0.11690(5) 0.0234(2) Uani 1 1 d . . .
C18 C 0.80818(9) 0.79830(14) 0.02354(6) 0.0229(3) Uani 1 1 d . . .
C19 C 0.71285(9) 0.79024(14) 0.00269(6) 0.0230(3) Uani 1 1 d . . .
C20 C 0.67309(10) 0.74333(14) -0.05185(6) 0.0254(3) Uani 1 1 d . . .
C21 C 0.57819(10) 0.74070(14) -0.05311(6) 0.0247(3) Uani 1 1 d . . .
C22 C 0.55622(9) 0.78743(13) 0.00035(6) 0.0224(3) Uani 1 1 d . . .
N23 N 0.63960(8) 0.81879(12) 0.03240(5) 0.0227(2) Uani 1 1 d . . .
C24 C 0.46595(9) 0.79882(13) 0.01566(5) 0.0222(3) Uani 1 1 d . . .
C25 C 0.25974(11) 0.83524(15) 0.04932(6) 0.0321(3) Uani 1 1 d . . .
C26 C 0.18942(13) 0.7938(2) 0.03164(8) 0.0448(4) Uani 1 1 d . . .
C27 C 0.27684(11) 1.01995(15) 0.14853(6) 0.0291(3) Uani 1 1 d . . .
C28 C 0.20997(12) 1.06131(18) 0.16220(7) 0.0382(4) Uani 1 1 d . . .
C29 C 0.43142(9) 1.11123(15) 0.22916(6) 0.0248(3) Uani 1 1 d . . .
C30 C 0.40452(11) 1.04254(17) 0.27527(6) 0.0321(3) Uani 1 1 d . . .
C31 C 0.34324(11) 1.10159(18) 0.30827(7) 0.0371(4) Uani 1 1 d . . .
C32 C 0.31019(10) 1.22882(17) 0.29654(7) 0.0353(4) Uani 1 1 d . . .
C33 C 0.33765(10) 1.29916(17) 0.25147(7) 0.0335(3) Uani 1 1 d . . .
C34 C 0.39838(10) 1.24058(16) 0.21781(6) 0.0292(3) Uani 1 1 d . . .
C35 C 0.91787(9) 1.04040(14) 0.25398(6) 0.0245(3) Uani 1 1 d . . .
C36 C 0.98564(10) 1.12940(16) 0.23907(7) 0.0302(3) Uani 1 1 d . . .
C37 C 1.06015(11) 1.16855(17) 0.27851(7) 0.0346(3) Uani 1 1 d . . .
C38 C 1.06742(11) 1.12196(16) 0.33357(7) 0.0339(3) Uani 1 1 d . . .
C39 C 0.99915(11) 1.03846(16) 0.34922(7) 0.0338(3) Uani 1 1 d . . .
C40 C 0.92555(10) 0.99593(16) 0.30990(6) 0.0285(3) Uani 1 1 d . . .
C41 C 0.87521(9) 0.75162(15) -0.01526(6) 0.0254(3) Uani 1 1 d . . .
C42 C 0.88190(11) 0.61687(17) -0.02830(7) 0.0355(4) Uani 1 1 d . . .
C43 C 0.94457(12) 0.5742(2) -0.06431(7) 0.0414(4) Uani 1 1 d . . .
C44 C 1.00021(11) 0.6661(2) -0.08761(7) 0.0396(4) Uani 1 1 d . . .
C45 C 0.99406(11) 0.7991(2) -0.07505(7) 0.0379(4) Uani 1 1 d . . .
C46 C 0.93162(10) 0.84288(18) -0.03907(6) 0.0321(3) Uani 1 1 d . . .
C47 C 0.39046(9) 0.73540(13) -0.02486(6) 0.0224(3) Uani 1 1 d . . .
C48 C 0.33694(11) 0.80908(16) -0.06657(6) 0.0322(3) Uani 1 1 d . . .
C49 C 0.26817(11) 0.74754(17) -0.10413(7) 0.0341(3) Uani 1 1 d . . .
C50 C 0.25323(10) 0.61151(16) -0.10075(7) 0.0307(3) Uani 1 1 d . . .
C51 C 0.30680(11) 0.53727(16) -0.05985(7) 0.0344(3) Uani 1 1 d . . .
C52 C 0.37499(10) 0.59859(15) -0.02193(7) 0.0301(3) Uani 1 1 d . . .
H53 H 0.5926(11) 1.1703(17) 0.2886(7) 0.035(4) Uiso 1 1 d . . .
H54 H 0.7731(11) 1.1536(15) 0.2999(7) 0.029(4) Uiso 1 1 d . . .
H55 H 0.6586(13) 0.949(2) 0.1590(8) 0.052(6) Uiso 1 1 d . . .
H56 H 1.0083(11) 0.9000(16) 0.1807(7) 0.032(4) Uiso 1 1 d . . .
H57 H 0.9956(11) 0.8011(15) 0.0789(7) 0.027(4) Uiso 1 1 d . . .
H58 H 0.7107(11) 0.7195(16) -0.0823(7) 0.031(4) Uiso 1 1 d . . .
H59 H 0.5311(10) 0.7198(14) -0.0853(6) 0.021(4) Uiso 1 1 d . . .
H60 H 0.6452(13) 0.8447(19) 0.0678(9) 0.048(6) Uiso 1 1 d . . .
H61 H 0.1279(17) 0.760(2) 0.0117(10) 0.077(7) Uiso 1 1 d . . .
H62 H 0.1497(19) 1.111(3) 0.1761(12) 0.106(9) Uiso 1 1 d . . .
H63 H 0.4268(11) 0.9546(18) 0.2822(7) 0.032(4) Uiso 1 1 d . . .
H64 H 0.3272(12) 1.0510(19) 0.3398(8) 0.046(5) Uiso 1 1 d . . .
H65 H 0.2692(12) 1.2707(17) 0.3214(7) 0.041(5) Uiso 1 1 d . . .
H66 H 0.3142(12) 1.3916(19) 0.2413(8) 0.044(5) Uiso 1 1 d . . .
H67 H 0.4165(12) 1.2908(18) 0.1869(8) 0.039(5) Uiso 1 1 d . . .
H68 H 0.9804(11) 1.1632(16) 0.1997(8) 0.034(4) Uiso 1 1 d . . .
H69 H 1.1075(13) 1.2284(18) 0.2654(7) 0.043(5) Uiso 1 1 d . . .
H70 H 1.1211(12) 1.1476(17) 0.3619(7) 0.034(4) Uiso 1 1 d . . .
H71 H 1.0017(13) 1.0109(19) 0.3879(9) 0.052(6) Uiso 1 1 d . . .
H72 H 0.8829(12) 0.9348(18) 0.3208(7) 0.040(5) Uiso 1 1 d . . .
H73 H 0.8436(12) 0.5521(18) -0.0118(7) 0.041(5) Uiso 1 1 d . . .
H74 H 0.9527(13) 0.479(2) -0.0704(8) 0.056(6) Uiso 1 1 d . . .
H75 H 1.0408(13) 0.6331(19) -0.1135(8) 0.049(5) Uiso 1 1 d . . .
H76 H 1.0319(13) 0.867(2) -0.0918(8) 0.051(5) Uiso 1 1 d . . .
H77 H 0.9250(12) 0.941(2) -0.0318(7) 0.043(5) Uiso 1 1 d . . .
H78 H 0.3473(13) 0.908(2) -0.0691(8) 0.051(5) Uiso 1 1 d . . .
H79 H 0.2275(14) 0.803(2) -0.1324(9) 0.057(6) Uiso 1 1 d . . .
H80 H 0.2041(11) 0.5690(16) -0.1285(7) 0.030(4) Uiso 1 1 d . . .
H81 H 0.2970(12) 0.4420(19) -0.0577(8) 0.045(5) Uiso 1 1 d . . .
H82 H 0.4138(12) 0.5493(19) 0.0077(8) 0.044(5) 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 0.0033 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'
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
C2 N1 C5 106.62(11) . . ?
N1 C2 C24 124.94(12) . . ?
N1 C2 C3 110.41(11) . . ?
C24 C2 C3 124.57(12) . . ?
C4 C3 C25 123.80(12) . . ?
C4 C3 C2 106.31(12) . . ?
C25 C3 C2 129.82(12) . . ?
C3 C4 C27 123.21(12) . . ?
C3 C4 C5 106.13(11) . . ?
C27 C4 C5 130.61(13) . . ?
N1 C5 C6 125.39(12) . . ?
N1 C5 C4 110.40(12) . . ?
C6 C5 C4 124.17(12) . . ?
C7 C6 C5 125.82(12) . . ?
C7 C6 C29 115.18(12) . . ?
C5 C6 C29 118.97(12) . . ?
N11 C7 C6 127.65(13) . . ?
N11 C7 C8 106.77(12) . . ?
C6 C7 C8 125.56(12) . . ?
C9 C8 C7 108.40(13) . . ?
C8 C9 C10 107.81(13) . . ?
N11 C10 C12 126.30(12) . . ?
N11 C10 C9 106.90(11) . . ?
C12 C10 C9 126.75(13) . . ?
C10 N11 C7 110.11(12) . . ?
C10 C12 C13 124.83(12) . . ?
C10 C12 C35 116.55(12) . . ?
C13 C12 C35 118.57(11) . . ?
N17 C13 C12 125.47(12) . . ?
N17 C13 C14 110.84(12) . . ?
C12 C13 C14 123.68(12) . . ?
C15 C14 C13 106.58(12) . . ?
C14 C15 C16 106.68(12) . . ?
N17 C16 C18 125.89(12) . . ?
N17 C16 C15 110.51(12) . . ?
C18 C16 C15 123.60(12) . . ?
C13 N17 C16 105.33(11) . . ?
C19 C18 C16 125.02(12) . . ?
C19 C18 C41 116.45(12) . . ?
C16 C18 C41 118.51(12) . . ?
N23 C19 C18 126.06(12) . . ?
N23 C19 C20 107.03(12) . . ?
C18 C19 C20 126.81(12) . . ?
C21 C20 C19 107.91(12) . . ?
C20 C21 C22 108.21(12) . . ?
N23 C22 C24 127.70(12) . . ?
N23 C22 C21 106.86(11) . . ?
C24 C22 C21 125.44(12) . . ?
C22 N23 C19 109.94(12) . . ?
C22 C24 C2 124.99(12) . . ?
C22 C24 C47 114.75(11) . . ?
C2 C24 C47 120.26(11) . . ?
C26 C25 C3 174.77(17) . . ?
C28 C27 C4 173.87(16) . . ?
C34 C29 C30 119.20(13) . . ?
C34 C29 C6 120.77(13) . . ?
C30 C29 C6 120.02(13) . . ?
C31 C30 C29 119.99(15) . . ?
C32 C31 C30 120.52(16) . . ?
C31 C32 C33 120.10(14) . . ?
C32 C33 C34 119.90(15) . . ?
C33 C34 C29 120.27(15) . . ?
C40 C35 C36 118.29(13) . . ?
C40 C35 C12 121.00(12) . . ?
C36 C35 C12 120.69(12) . . ?
C37 C36 C35 120.73(14) . . ?
C38 C37 C36 120.20(15) . . ?
C39 C38 C37 119.51(15) . . ?
C38 C39 C40 120.86(15) . . ?
C39 C40 C35 120.35(14) . . ?
C42 C41 C46 118.94(14) . . ?
C42 C41 C18 120.67(13) . . ?
C46 C41 C18 120.39(13) . . ?
C41 C42 C43 120.34(16) . . ?
C44 C43 C42 120.02(17) . . ?
C45 C44 C43 120.06(15) . . ?
C44 C45 C46 120.37(16) . . ?
C41 C46 C45 120.27(16) . . ?
C48 C47 C52 118.77(13) . . ?
C48 C47 C24 121.70(12) . . ?
C52 C47 C24 119.50(12) . . ?
C47 C48 C49 120.58(14) . . ?
C50 C49 C48 120.16(15) . . ?
C51 C50 C49 119.65(14) . . ?
C50 C51 C52 120.36(15) . . ?
C51 C52 C47 120.47(14) . . ?
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
N1 C2 1.3667(17) . ?
N1 C5 1.3668(17) . ?
C2 C24 1.4073(18) . ?
C2 C3 1.4621(18) . ?
C3 C4 1.3727(19) . ?
C3 C25 1.458(2) . ?
C4 C27 1.454(2) . ?
C4 C5 1.4643(18) . ?
C5 C6 1.4095(19) . ?
C6 C7 1.4003(18) . ?
C6 C29 1.4967(18) . ?
C7 N11 1.3779(17) . ?
C7 C8 1.430(2) . ?
C8 C9 1.365(2) . ?
C9 C10 1.4375(19) . ?
C10 N11 1.3739(17) . ?
C10 C12 1.4027(18) . ?
C12 C13 1.4098(19) . ?
C12 C35 1.4947(19) . ?
C13 N17 1.3694(17) . ?
C13 C14 1.4590(18) . ?
C14 C15 1.345(2) . ?
C15 C16 1.4614(19) . ?
C16 N17 1.3738(17) . ?
C16 C18 1.4022(19) . ?
C18 C19 1.4012(18) . ?
C18 C41 1.4974(18) . ?
C19 N23 1.3766(17) . ?
C19 C20 1.4295(19) . ?
C20 C21 1.3649(19) . ?
C21 C22 1.4314(18) . ?
C22 N23 1.3735(17) . ?
C22 C24 1.4015(18) . ?
C24 C47 1.4981(19) . ?
C25 C26 1.125(2) . ?
C27 C28 1.136(2) . ?
C29 C34 1.393(2) . ?
C29 C30 1.394(2) . ?
C30 C31 1.389(2) . ?
C31 C32 1.375(2) . ?
C32 C33 1.385(2) . ?
C33 C34 1.392(2) . ?
C35 C40 1.396(2) . ?
C35 C36 1.402(2) . ?
C36 C37 1.388(2) . ?
C37 C38 1.384(2) . ?
C38 C39 1.379(2) . ?
C39 C40 1.387(2) . ?
C41 C42 1.390(2) . ?
C41 C46 1.392(2) . ?
C42 C43 1.393(2) . ?
C43 C44 1.384(3) . ?
C44 C45 1.370(3) . ?
C45 C46 1.393(2) . ?
C47 C48 1.388(2) . ?
C47 C52 1.390(2) . ?
C48 C49 1.390(2) . ?
C49 C50 1.382(2) . ?
C50 C51 1.379(2) . ?
C51 C52 1.388(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21198926
