#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:46:54 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180315 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/29/7152930.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_7152930
loop_
_publ_author_name
'Akhigbe, Joshua'
'Haskoor, John'
'Krause, Jeanette A.'
'Zeller, Matthias'
'Brückner, Christian'
_publ_section_title
;
 Formation, structure, and reactivity of meso-tetraaryl-chlorolactones,
 -porpholactams, and -chlorolactams, porphyrin and chlorin analogues
 incorporating oxazolone or imidazolone moieties.
;
_journal_issue                   22
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3616
_journal_page_last               3628
_journal_paper_doi               10.1039/c3ob40138c
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C43 H30 N4 O2'
_chemical_formula_weight         634.71
_chemical_name_systematic
;
?
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/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                 101.024(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.016(3)
_cell_length_b                   6.7826(18)
_cell_length_c                   21.878(6)
_cell_measurement_reflns_used    3044
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      2.82
_cell_volume                     1604.5(8)
_computing_cell_refinement       'Bruker SAINT v7.60A'
_computing_data_collection       'Bruker APEX2 v2010.3.0'
_computing_data_reduction        'Bruker SAINT v7.60A'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker AXS APEXII CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.88560
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14751
_diffrn_reflns_theta_full        33.53
_diffrn_reflns_theta_max         33.53
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Sheldrick, 2008)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3227
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0578P)²+0.2585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                2278
_reflns_number_total             3227
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ob40138c.txt
_cod_data_source_block           uconn001_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1604.6(7)
_cod_original_sg_symbol_H-M      P2/n
_cod_database_code               7152930
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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
C1 C 0.24996(15) 0.4563(2) 0.62271(7) 0.0358(4) Uani 1 1 d . . .
C2 C 0.15667(15) 0.3133(2) 0.61743(7) 0.0344(4) Uani 1 1 d D . .
C3 C 0.1691(15) 0.147(2) 0.6639(8) 0.0465(13) Uani 0.50 1 d PD A 1
H3A H 0.1737 0.1966 0.7068 0.056 Uiso 0.50 1 calc PR A 1
H3B H 0.2432 0.0655 0.6624 0.056 Uiso 0.50 1 calc PR A 1
C4 C 0.0465(15) 0.026(2) 0.6411(7) 0.0428(13) Uani 0.50 1 d PD A 1
H4A H 0.0643 -0.1096 0.6283 0.051 Uiso 0.50 1 calc PR A 1
H4B H -0.0046 0.0188 0.6737 0.051 Uiso 0.50 1 calc PR A 1
C3A C 0.155(3) 0.138(6) 0.658(2) 0.0465(13) Uani 0.249(4) 1 d PD A 2
O1A O 0.2165(5) 0.0511(9) 0.6993(2) 0.0534(19) Uani 0.249(4) 1 d PD A 2
O2A O 0.046(2) 0.041(4) 0.6341(12) 0.0428(13) Uani 0.249(4) 1 d PD A 2
C3B C 0.057(3) 0.056(5) 0.6430(17) 0.0428(13) Uani 0.251(4) 1 d PD A 3
O1B O 0.0587(5) -0.0845(8) 0.6740(3) 0.061(2) Uani 0.251(4) 1 d PD A 3
O2B O 0.162(2) 0.169(4) 0.6597(13) 0.0465(13) Uani 0.251(4) 1 d PD A 3
C5 C -0.01535(14) 0.1481(2) 0.58621(7) 0.0327(4) Uani 1 1 d D . .
C6 C -0.13034(14) 0.0862(2) 0.55317(8) 0.0335(4) Uani 1 1 d . A .
C7 C -0.19494(15) 0.1715(2) 0.49809(8) 0.0342(4) Uani 1 1 d . . .
C8 C -0.31650(15) 0.1197(3) 0.46627(8) 0.0417(4) Uani 1 1 d . A .
H8 H -0.3659 0.0156 0.4772 0.050 Uiso 1 1 calc R . .
C9 C -0.34916(16) 0.2474(3) 0.41701(8) 0.0417(4) Uani 1 1 d . . .
H9 H -0.4250 0.2463 0.3878 0.050 Uiso 1 1 calc R A .
C10 C -0.24955(14) 0.3813(2) 0.41746(8) 0.0356(4) Uani 1 1 d . . .
C11 C 0.36149(15) 0.4335(3) 0.67368(8) 0.0377(4) Uani 1 1 d . . .
C12 C 0.43872(16) 0.2705(3) 0.67541(8) 0.0416(4) Uani 1 1 d . A .
H12 H 0.4209 0.1721 0.6441 0.050 Uiso 1 1 calc R . .
C13 C 0.54196(17) 0.2508(3) 0.72283(10) 0.0517(5) Uani 1 1 d . . .
H13 H 0.5938 0.1385 0.7237 0.062 Uiso 1 1 calc R A .
C14 C 0.56944(18) 0.3901(3) 0.76786(9) 0.0571(6) Uani 1 1 d . A .
H14 H 0.6402 0.3750 0.8000 0.068 Uiso 1 1 calc R . .
C15 C 0.4951(2) 0.5526(3) 0.76702(9) 0.0572(6) Uani 1 1 d . . .
H15 H 0.5147 0.6498 0.7986 0.069 Uiso 1 1 calc R A .
C16 C 0.39071(17) 0.5763(3) 0.72001(8) 0.0478(5) Uani 1 1 d . A .
H16 H 0.3397 0.6894 0.7196 0.057 Uiso 1 1 calc R . .
C17 C -0.19518(14) -0.0793(2) 0.57955(8) 0.0347(4) Uani 1 1 d . . .
C18 C -0.24083(18) -0.0515(3) 0.63391(9) 0.0506(5) Uani 1 1 d . A .
H18 H -0.2281 0.0712 0.6551 0.061 Uiso 1 1 calc R . .
C19 C -0.30455(18) -0.2001(3) 0.65752(9) 0.0537(5) Uani 1 1 d . . .
H19 H -0.3346 -0.1788 0.6949 0.064 Uiso 1 1 calc R A .
C20 C -0.32472(16) -0.3772(3) 0.62754(9) 0.0458(5) Uani 1 1 d . A .
H20 H -0.3694 -0.4783 0.6436 0.055 Uiso 1 1 calc R . .
C21 C -0.2798(2) -0.4073(3) 0.57415(11) 0.0587(6) Uani 1 1 d . . .
H21 H -0.2932 -0.5301 0.5531 0.070 Uiso 1 1 calc R A .
C22 C -0.2143(2) -0.2588(3) 0.55051(10) 0.0538(5) Uani 1 1 d . A .
H22 H -0.1826 -0.2823 0.5137 0.065 Uiso 1 1 calc R . .
N1 N 0.05093(12) 0.30754(19) 0.57374(6) 0.0332(3) Uani 1 1 d . A .
N2 N -0.15737(12) 0.32872(19) 0.46640(6) 0.0337(3) Uani 1 1 d . A .
H2 H -0.0849 0.3870 0.4761 0.040 Uiso 1 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 -0.0020 0.0027 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175.'
H H 0.0000 0.0000 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175.'
N N -0.0031 0.0054 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175.'
O O -0.0042 0.0099 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175.'
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
C2 C1 C10 125.09(15) . 3_566
C2 C1 C11 118.25(14) . .
C10 C1 C11 116.63(14) 3_566 .
O2B C2 N1 112.6(7) . .
O2B C2 C1 120.9(7) . .
N1 C2 C1 126.46(15) . .
N1 C2 C3A 106.8(7) . .
C1 C2 C3A 126.7(7) . .
N1 C2 C3 114.1(5) . .
C1 C2 C3 119.5(5) . .
C2 C3 C4 102.4(8) . .
C2 C3 H3A 111.3 . .
C4 C3 H3A 111.3 . .
C2 C3 H3B 111.3 . .
C4 C3 H3B 111.3 . .
H3A C3 H3B 109.2 . .
C5 C4 C3 101.2(8) . .
C5 C4 H4A 111.5 . .
C3 C4 H4A 111.5 . .
C5 C4 H4B 111.5 . .
C3 C4 H4B 111.5 . .
H4A C4 H4B 109.3 . .
O1A C3A O2A 112.3(15) . .
O1A C3A C2 141.9(16) . .
O2A C3A C2 105.6(11) . .
C5 O2A C3A 107.7(12) . .
O1B C3B O2B 112.6(15) . .
O1B C3B C5 140.8(16) . .
O2B C3B C5 106.2(11) . .
C2 O2B C3B 107.4(12) . .
O2A C5 N1 112.2(7) . .
O2A C5 C6 120.7(7) . .
N1 C5 C6 127.06(14) . .
N1 C5 C3B 106.1(6) . .
C6 C5 C3B 126.8(7) . .
N1 C5 C4 114.7(5) . .
C6 C5 C4 118.2(5) . .
C5 C6 C7 125.57(15) . .
C5 C6 C17 118.40(14) . .
C7 C6 C17 115.96(14) . .
N2 C7 C6 126.86(15) . .
N2 C7 C8 106.78(14) . .
C6 C7 C8 126.24(15) . .
C9 C8 C7 107.88(15) . .
C9 C8 H8 126.1 . .
C7 C8 H8 126.1 . .
C8 C9 C10 108.09(15) . .
C8 C9 H9 126.0 . .
C10 C9 H9 126.0 . .
N2 C10 C1 127.07(14) . 3_566
N2 C10 C9 107.07(14) . .
C1 C10 C9 125.76(15) 3_566 .
C12 C11 C16 118.51(16) . .
C12 C11 C1 120.75(15) . .
C16 C11 C1 120.74(16) . .
C11 C12 C13 120.32(18) . .
C11 C12 H12 119.8 . .
C13 C12 H12 119.8 . .
C14 C13 C12 120.8(2) . .
C14 C13 H13 119.6 . .
C12 C13 H13 119.6 . .
C13 C14 C15 120.02(18) . .
C13 C14 H14 120.0 . .
C15 C14 H14 120.0 . .
C14 C15 C16 120.5(2) . .
C14 C15 H15 119.8 . .
C16 C15 H15 119.8 . .
C11 C16 C15 119.89(19) . .
C11 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
C22 C17 C18 117.93(16) . .
C22 C17 C6 121.84(15) . .
C18 C17 C6 120.20(15) . .
C19 C18 C17 120.86(18) . .
C19 C18 H18 119.6 . .
C17 C18 H18 119.6 . .
C20 C19 C18 120.58(18) . .
C20 C19 H19 119.7 . .
C18 C19 H19 119.7 . .
C19 C20 C21 119.26(17) . .
C19 C20 H20 120.4 . .
C21 C20 H20 120.4 . .
C20 C21 C22 120.40(18) . .
C20 C21 H21 119.8 . .
C22 C21 H21 119.8 . .
C17 C22 C21 120.95(18) . .
C17 C22 H22 119.5 . .
C21 C22 H22 119.5 . .
C2 N1 C5 107.60(13) . .
C10 N2 C7 110.15(13) . .
C10 N2 H2 124.9 . .
C7 N2 H2 124.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.402(2) .
C1 C10 1.409(2) 3_566
C1 C11 1.501(2) .
C2 O2B 1.338(16) .
C2 N1 1.359(2) .
C2 C3A 1.483(17) .
C2 C3 1.510(13) .
C3 C4 1.577(16) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.511(12) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C3A O1A 1.182(15) .
C3A O2A 1.382(17) .
O2A C5 1.346(16) .
C3B O1B 1.169(15) .
C3B O2B 1.376(17) .
C3B C5 1.481(17) .
C5 N1 1.362(2) .
C5 C6 1.398(2) .
C6 C7 1.402(2) .
C6 C17 1.504(2) .
C7 N2 1.378(2) .
C7 C8 1.430(2) .
C8 C9 1.376(3) .
C8 H8 0.9500 .
C9 C10 1.423(2) .
C9 H9 0.9500 .
C10 N2 1.375(2) .
C10 C1 1.409(2) 3_566
C11 C12 1.391(2) .
C11 C16 1.394(3) .
C12 C13 1.392(3) .
C12 H12 0.9500 .
C13 C14 1.357(3) .
C13 H13 0.9500 .
C14 C15 1.371(3) .
C14 H14 0.9500 .
C15 C16 1.398(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 C22 1.371(2) .
C17 C18 1.390(2) .
C18 C19 1.383(3) .
C18 H18 0.9500 .
C19 C20 1.366(3) .
C19 H19 0.9500 .
C20 C21 1.368(3) .
C20 H20 0.9500 .
C21 C22 1.395(3) .
C21 H21 0.9500 .
C22 H22 0.9500 .
N2 H2 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_4
C10 C1 C2 O2B -177(2) 3_566 .
C11 C1 C2 O2B 5(2) . .
C10 C1 C2 N1 -0.6(3) 3_566 .
C11 C1 C2 N1 -178.64(15) . .
C10 C1 C2 C3A 179(4) 3_566 .
C11 C1 C2 C3A 1(4) . .
C10 C1 C2 C3 -180.0(10) 3_566 .
C11 C1 C2 C3 2.0(10) . .
O2B C2 C3 C4 63(26) . .
N1 C2 C3 C4 0.2(13) . .
C1 C2 C3 C4 179.6(8) . .
C3A C2 C3 C4 -9(26) . .
C2 C3 C4 C5 -1.1(13) . .
O2B C2 C3A O1A -41(22) . .
N1 C2 C3A O1A 173(9) . .
C1 C2 C3A O1A -6(12) . .
C3 C2 C3A O1A -15(17) . .
O2B C2 C3A O2A 146(35) . .
N1 C2 C3A O2A 0(5) . .
C1 C2 C3A O2A -179(2) . .
C3 C2 C3A O2A 172(31) . .
O1A C3A O2A C5 -178(5) . .
C2 C3A O2A C5 -3(6) . .
N1 C2 O2B C3B 2(4) . .
C1 C2 O2B C3B 179(3) . .
C3A C2 O2B C3B -34(29) . .
C3 C2 O2B C3B -116(28) . .
O1B C3B O2B C2 173(4) . .
C5 C3B O2B C2 -1(5) . .
C3A O2A C5 N1 4(4) . .
C3A O2A C5 C6 -179(4) . .
C3A O2A C5 C3B -37(20) . .
C3A O2A C5 C4 -138(33) . .
O1B C3B C5 O2A -31(15) . .
O2B C3B C5 O2A 140(25) . .
O1B C3B C5 N1 -172(7) . .
O2B C3B C5 N1 0(4) . .
O1B C3B C5 C6 10(9) . .
O2B C3B C5 C6 -179(2) . .
O1B C3B C5 C4 -11(10) . .
O2B C3B C5 C4 161(20) . .
C3 C4 C5 O2A 41(31) . .
C3 C4 C5 N1 1.8(12) . .
C3 C4 C5 C6 -179.6(8) . .
C3 C4 C5 C3B -18(16) . .
O2A C5 C6 C7 -171.5(19) . .
N1 C5 C6 C7 4.5(3) . .
C3B C5 C6 C7 -177(3) . .
C4 C5 C6 C7 -173.9(9) . .
O2A C5 C6 C17 11.7(19) . .
N1 C5 C6 C17 -172.32(14) . .
C3B C5 C6 C17 6(3) . .
C4 C5 C6 C17 9.3(9) . .
C5 C6 C7 N2 0.6(3) . .
C17 C6 C7 N2 177.50(14) . .
C5 C6 C7 C8 -175.01(16) . .
C17 C6 C7 C8 1.9(2) . .
N2 C7 C8 C9 -0.60(19) . .
C6 C7 C8 C9 175.72(16) . .
C7 C8 C9 C10 -0.4(2) . .
C8 C9 C10 N2 1.30(19) . .
C8 C9 C10 C1 -175.21(16) . 3_566
C2 C1 C11 C12 62.1(2) . .
C10 C1 C11 C12 -116.13(18) 3_566 .
C2 C1 C11 C16 -118.57(18) . .
C10 C1 C11 C16 63.2(2) 3_566 .
C16 C11 C12 C13 0.6(2) . .
C1 C11 C12 C13 179.95(16) . .
C11 C12 C13 C14 -0.3(3) . .
C12 C13 C14 C15 0.0(3) . .
C13 C14 C15 C16 0.0(3) . .
C12 C11 C16 C15 -0.5(3) . .
C1 C11 C16 C15 -179.88(16) . .
C14 C15 C16 C11 0.2(3) . .
C5 C6 C17 C22 -113.6(2) . .
C7 C6 C17 C22 69.2(2) . .
C5 C6 C17 C18 68.2(2) . .
C7 C6 C17 C18 -108.93(19) . .
C22 C17 C18 C19 -0.6(3) . .
C6 C17 C18 C19 177.66(17) . .
C17 C18 C19 C20 -0.5(3) . .
C18 C19 C20 C21 0.8(3) . .
C19 C20 C21 C22 -0.1(3) . .
C18 C17 C22 C21 1.3(3) . .
C6 C17 C22 C21 -176.94(18) . .
C20 C21 C22 C17 -0.9(3) . .
O2B C2 N1 C5 -2(2) . .
C1 C2 N1 C5 -178.48(15) . .
C3A C2 N1 C5 2(3) . .
C3 C2 N1 C5 0.9(10) . .
O2A C5 N1 C2 -3.9(18) . .
C6 C5 N1 C2 179.80(15) . .
C3B C5 N1 C2 1(2) . .
C4 C5 N1 C2 -1.7(9) . .
C1 C10 N2 C7 174.75(16) 3_566 .
C9 C10 N2 C7 -1.70(18) . .
C6 C7 N2 C10 -174.84(16) . .
C8 C7 N2 C10 1.44(18) . .
