#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/05/1520552.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_1520552
loop_
_publ_author_name
'Saltsman, Irena'
'Goldberg, Israel'
'Gross, Zeev'
_publ_section_title
;
 Porphyrins and Corroles with 2,6-Pyrimidyl Substituents.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3214
_journal_page_last               3217
_journal_paper_doi               10.1021/acs.orglett.5b01297
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C36 H22 N12'
_chemical_formula_sum            'C36 H22 N12'
_chemical_formula_weight         622.66
_chemical_name_systematic
; 
 ? 
;
_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                 90.677(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3809(6)
_cell_length_b                   11.5149(6)
_cell_length_c                   17.7975(8)
_cell_measurement_reflns_used    4611
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      1.76
_cell_volume                     3151.9(2)
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_collection       'Apex2, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 1.75
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '1 deg. φ and 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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20359
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_platon_squeeze_details
;
 four molecules of the disordered MeOH solvent.
;
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0451
_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)+(0.0594P)²+2.0882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                4611
_reflns_number_total             5754
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01297_si_002.cif
_cod_data_source_block           compound-9
_cod_depositor_comments
'Adding full bibliography for 1520552--1520554.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1520552
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
N1 N 0.55092(9) 0.66187(14) 0.96820(9) 0.0180(3) Uani 1 1 d .
H1 H 0.5311 0.5854 0.9826 0.022 Uiso 1 1 d R
N2 N 0.37847(9) 0.53751(13) 0.96216(8) 0.0170(3) Uani 1 1 d .
N3 N 0.02881(10) 0.47489(14) 1.11010(8) 0.0184(3) Uani 1 1 d .
H3 H 0.0348 0.5859 1.0127 0.022 Uiso 1 1 d R
N4 N 0.06463(10) 0.65906(13) 1.01084(8) 0.0178(3) Uani 1 1 d .
N5 N 0.80942(10) 0.71332(14) 1.10454(9) 0.0195(4) Uani 1 1 d .
N6 N 0.81824(10) 0.77203(15) 0.97638(9) 0.0211(4) Uani 1 1 d .
N7 N 0.00850(11) 0.90512(15) 0.82830(9) 0.0237(4) Uani 1 1 d .
N8 N 0.34133(12) 0.92167(16) 0.91750(9) 0.0289(4) Uani 1 1 d .
N9 N 0.12451(11) 0.79500(16) 0.77590(9) 0.0273(4) Uani 1 1 d .
N10 N 0.38072(12) 0.83944(16) 0.80093(9) 0.0314(4) Uani 1 1 d .
N11 N 0.13168(13) 0.81437(17) 1.22469(10) 0.0363(5) Uani 1 1 d .
N12 N 0.23251(12) 0.65937(18) 1.23145(11) 0.0366(5) Uani 1 1 d .
C13 C 0.30512(11) 0.46979(17) 0.95803(10) 0.0173(4) Uani 1 1 d .
C14 C 0.49897(12) 0.74481(17) 0.93480(10) 0.0182(4) Uani 1 1 d .
C15 C 0.78178(11) 0.71307(16) 1.03289(10) 0.0174(4) Uani 1 1 d .
C16 C 0.07437(12) 0.54285(17) 1.16010(10) 0.0187(4) Uani 1 1 d .
C17 C 0.35627(11) 0.63930(16) 0.92794(10) 0.0162(4) Uani 1 1 d .
C18 C 0.37426(11) 0.83789(16) 0.87516(10) 0.0180(4) Uani 1 1 d .
C19 C 0.07334(11) 0.73334(17) 0.95117(10) 0.0183(4) Uani 1 1 d .
C20 C 0.63296(11) 0.70597(17) 0.98063(10) 0.0182(4) Uani 1 1 d .
C21 C 0.41097(12) 0.73390(16) 0.91538(10) 0.0164(4) Uani 1 1 d .
C22 C 0.70067(11) 0.64574(17) 1.01625(10) 0.0177(4) Uani 1 1 d .
C23 C 0.10762(11) 0.70357(17) 1.07241(10) 0.0192(4) Uani 1 1 d .
C24 C 0.23433(12) 0.53307(17) 0.92195(10) 0.0185(4) Uani 1 1 d .
H24 H 0.1767 0.5058 0.9135 0.022 Uiso 1 1 calc R
C25 C 0.63231(12) 0.82254(17) 0.95257(11) 0.0212(4) Uani 1 1 d .
H25 H 0.6801 0.8748 0.9532 0.025 Uiso 1 1 calc R
C26 C 0.04245(11) 0.71620(17) 0.87812(10) 0.0178(4) Uani 1 1 d .
C27 C 0.05962(11) 0.81202(17) 0.82400(10) 0.0183(4) Uani 1 1 d .
C28 C 0.11261(12) 0.64956(17) 1.14264(10) 0.0189(4) Uani 1 1 d .
C29 C 0.00329(12) 0.37932(17) 1.15030(10) 0.0183(4) Uani 1 1 d .
C30 C 0.16202(12) 0.71174(18) 1.20339(10) 0.0213(4) Uani 1 1 d .
C31 C 0.55165(12) 0.84538(17) 0.92487(11) 0.0211(4) Uani 1 1 d .
H31 H 0.5333 0.9164 0.9026 0.025 Uiso 1 1 calc R
C32 C 0.26603(11) 0.63755(17) 0.90281(10) 0.0178(4) Uani 1 1 d .
H32 H 0.2355 0.6983 0.8778 0.021 Uiso 1 1 calc R
C33 C 0.12409(12) 0.83013(17) 0.97688(11) 0.0220(4) Uani 1 1 d .
H33 H 0.1401 0.8957 0.9477 0.026 Uiso 1 1 calc R
C34 C 0.07662(12) 0.48950(18) 1.23413(11) 0.0235(4) Uani 1 1 d .
H34 H 0.1038 0.5197 1.2782 0.028 Uiso 1 1 calc R
C35 C 0.87882(12) 0.77967(18) 1.12043(11) 0.0222(4) Uani 1 1 d .
H35 H 0.9013 0.7804 1.1704 0.027 Uiso 1 1 calc R
C36 C 0.14533(12) 0.81184(17) 1.05037(11) 0.0220(4) Uani 1 1 d .
H36 H 0.1791 0.8619 1.0815 0.026 Uiso 1 1 calc R
C37 C 0.03277(12) 0.38919(18) 1.22791(11) 0.0233(4) Uani 1 1 d .
H37 H 0.0228 0.3347 1.2670 0.028 Uiso 1 1 calc R
C38 C 0.88634(12) 0.83929(18) 0.99433(11) 0.0228(4) Uani 1 1 d .
H38 H 0.9133 0.8833 0.9559 0.027 Uiso 1 1 calc R
C39 C 0.91879(12) 0.84694(18) 1.06684(11) 0.0239(4) Uani 1 1 d .
H39 H 0.9664 0.8962 1.0792 0.029 Uiso 1 1 calc R
C40 C 0.02358(14) 0.98888(19) 0.77780(11) 0.0284(5) Uani 1 1 d .
H40 H -0.0113 1.0569 0.7784 0.034 Uiso 1 1 calc R
C41 C 0.31840(14) 1.02863(19) 0.80451(12) 0.0292(5) Uani 1 1 d .
H41 H 0.2993 1.0969 0.7793 0.035 Uiso 1 1 calc R
C42 C 0.31308(15) 1.01658(19) 0.88056(12) 0.0334(5) Uani 1 1 d .
H42 H 0.2883 1.0781 0.9087 0.040 Uiso 1 1 calc R
C43 C 0.35279(16) 0.9365(2) 0.76679(12) 0.0379(6) Uani 1 1 d .
H43 H 0.3571 0.9414 0.7137 0.045 Uiso 1 1 calc R
C44 C 0.08778(16) 0.9796(2) 0.72523(12) 0.0360(5) Uani 1 1 d .
H44 H 0.0975 1.0394 0.6896 0.043 Uiso 1 1 calc R
C45 C 0.24899(14) 0.8214(2) 1.31268(12) 0.0334(5) Uani 1 1 d .
H45 H 0.2797 0.8600 1.3520 0.040 Uiso 1 1 calc R
C46 C 0.13732(15) 0.8807(2) 0.72618(12) 0.0340(5) Uani 1 1 d .
H46 H 0.1823 0.8725 0.6904 0.041 Uiso 1 1 calc R
C47 C 0.27456(15) 0.7161(2) 1.28678(13) 0.0391(6) Uani 1 1 d .
H47 H 0.3245 0.6810 1.3089 0.047 Uiso 1 1 calc R
C48 C 0.17711(18) 0.8692(2) 1.27945(14) 0.0447(6) Uani 1 1 d .
H48 H 0.1583 0.9437 1.2954 0.054 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 0.0033 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
C20 N1 C14 109.89(16) . .
C17 N2 C13 105.27(15) . .
C29 N3 C16 105.45(15) . .
C23 N4 C19 109.56(16) . .
C35 N5 C15 116.43(16) . .
C38 N6 C15 116.54(16) . .
C27 N7 C40 115.70(17) . .
C18 N8 C42 115.85(17) . .
C27 N9 C46 115.53(18) . .
C18 N10 C43 115.81(18) . .
C30 N11 C48 116.22(19) . .
C30 N12 C47 116.0(2) . .
N2 C13 C22 125.00(16) . 3_667
N2 C13 C24 110.47(16) . .
C22 C13 C24 124.52(17) 3_667 .
N1 C14 C21 126.86(17) . .
N1 C14 C31 106.82(15) . .
C21 C14 C31 126.32(17) . .
N5 C15 N6 125.58(17) . .
N5 C15 C22 116.38(16) . .
N6 C15 C22 117.97(16) . .
N3 C16 C28 124.76(17) . .
N3 C16 C34 110.71(17) . .
C28 C16 C34 124.53(17) . .
N2 C17 C21 126.48(16) . .
N2 C17 C32 111.04(16) . .
C21 C17 C32 122.46(17) . .
N10 C18 N8 126.09(18) . .
N10 C18 C21 116.96(17) . .
N8 C18 C21 116.89(16) . .
N4 C19 C26 126.80(18) . .
N4 C19 C33 107.21(16) . .
C26 C19 C33 125.93(17) . .
N1 C20 C22 124.55(18) . .
N1 C20 C25 106.70(16) . .
C22 C20 C25 128.72(17) . .
C17 C21 C14 127.87(17) . .
C17 C21 C18 118.33(15) . .
C14 C21 C18 113.79(16) . .
C20 C22 C13 124.48(17) . 3_667
C20 C22 C15 116.63(17) . .
C13 C22 C15 118.72(16) 3_667 .
N4 C23 C28 124.67(18) . .
N4 C23 C36 107.41(16) . .
C28 C23 C36 127.92(18) . .
C32 C24 C13 106.78(16) . .
C31 C25 C20 108.13(17) . .
C19 C26 C29 127.88(17) . 3_567
C19 C26 C27 115.93(17) . .
C29 C26 C27 116.18(16) 3_567 .
N7 C27 N9 126.89(18) . .
N7 C27 C26 116.71(16) . .
N9 C27 C26 116.40(17) . .
C23 C28 C16 124.81(17) . .
C23 C28 C30 117.09(17) . .
C16 C28 C30 118.10(17) . .
N3 C29 C26 126.04(17) . 3_567
N3 C29 C37 110.17(17) . .
C26 C29 C37 123.76(17) 3_567 .
N11 C30 N12 125.66(19) . .
N11 C30 C28 117.06(17) . .
N12 C30 C28 117.27(18) . .
C25 C31 C14 108.46(17) . .
C24 C32 C17 106.41(16) . .
C36 C33 C19 108.07(17) . .
C37 C34 C16 106.40(17) . .
N5 C35 C39 122.33(18) . .
C33 C36 C23 107.75(17) . .
C34 C37 C29 107.27(17) . .
N6 C38 C39 122.22(18) . .
C35 C39 C38 116.83(18) . .
N7 C40 C44 122.2(2) . .
C43 C41 C42 115.9(2) . .
N8 C42 C41 123.0(2) . .
N10 C43 C41 123.3(2) . .
C46 C44 C40 117.4(2) . .
C47 C45 C48 116.7(2) . .
N9 C46 C44 122.24(19) . .
N12 C47 C45 123.1(2) . .
N11 C48 C45 122.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C20 1.376(2) .
N1 C14 1.376(2) .
N2 C17 1.363(2) .
N2 C13 1.373(2) .
N3 C29 1.372(2) .
N3 C16 1.371(2) .
N4 C23 1.372(2) .
N4 C19 1.371(2) .
N5 C35 1.340(2) .
N5 C15 1.339(2) .
N6 C38 1.338(3) .
N6 C15 1.342(2) .
N7 C27 1.332(3) .
N7 C40 1.340(3) .
N8 C18 1.328(3) .
N8 C42 1.345(3) .
N9 C27 1.337(2) .
N9 C46 1.341(3) .
N10 C18 1.326(3) .
N10 C43 1.340(3) .
N11 C30 1.328(3) .
N11 C48 1.349(3) .
N12 C30 1.333(3) .
N12 C47 1.342(3) .
C13 C22 1.410(3) 3_667
C13 C24 1.453(3) .
C14 C21 1.399(3) .
C14 C31 1.426(3) .
C15 C22 1.496(3) .
C16 C28 1.399(3) .
C16 C34 1.454(3) .
C17 C21 1.396(3) .
C17 C32 1.453(2) .
C18 C21 1.502(3) .
C19 C26 1.393(3) .
C19 C33 1.433(3) .
C20 C22 1.397(3) .
C20 C25 1.432(3) .
C22 C13 1.410(3) 3_667
C23 C28 1.397(3) .
C23 C36 1.432(3) .
C24 C32 1.344(3) .
C25 C31 1.355(3) .
C26 C29 1.397(3) 3_567
C26 C27 1.490(3) .
C28 C30 1.497(3) .
C29 C26 1.397(3) 3_567
C29 C37 1.453(3) .
C33 C36 1.361(3) .
C34 C37 1.342(3) .
C35 C39 1.379(3) .
C38 C39 1.381(3) .
C40 C44 1.372(3) .
C41 C43 1.365(3) .
C41 C42 1.364(3) .
C44 C46 1.370(3) .
C45 C47 1.357(3) .
C45 C48 1.364(3) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.094 0.254 0.392 81 21 ' '
2 0.594 0.245 0.892 81 21 ' '
3 0.406 0.754 0.108 81 21 ' '
4 0.906 0.745 0.608 81 21 ' '
