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#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/39/4023913.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_4023913
loop_
_publ_author_name
'Zhan Zhang'
'Ji-Young Shin'
'David Dolphin'
_publ_contact_author_address
;Department of Chemistry,
University of British Columbia,
2036 Main Mall, Vancouver
BC V6T1Z1 Canada
;
_publ_contact_author_email       david.dolphin@ubc.ca
_publ_contact_author_fax         1-604-822-9678
_publ_contact_author_name        'David Dolphin'
_publ_contact_author_phone       1-604-822-4571
_publ_section_title
;
 Facile Synthesis of Unsubstituted β,β'-Linked
 Diformyldipyrromethanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9515
_journal_page_last               9517
_journal_paper_doi               10.1021/jo802114h
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C11 H10 N2 O2'
_chemical_formula_weight         202.21
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.8943(12)
_cell_length_b                   4.5121(3)
_cell_length_c                   11.5662(8)
_cell_measurement_reflns_used    2962
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.64
_cell_measurement_theta_min      2.78
_cell_volume                     986.05(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'area detector'
_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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7226
_diffrn_reflns_theta_full        27.84
_diffrn_reflns_theta_max         27.84
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0327
_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)+(0.0476P)²+0.0908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                2069
_reflns_number_total             2311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802114h_si_001_1.cif
_cod_data_source_block           compound3
_cod_database_code               4023913
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -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 0.30419(8) 1.4617(4) 0.51987(17) 0.0315(4) Uani 1 1 d . . .
H1 H 0.2814 1.5044 0.4486 0.038 Uiso 1 1 calc R . .
C2 C 0.26955(7) 1.2576(3) 0.59520(13) 0.0262(3) Uani 1 1 d . . .
C3 C 0.20511(7) 1.1125(3) 0.58039(13) 0.0265(3) Uani 1 1 d . . .
H3 H 0.1751 1.1267 0.5147 0.032 Uiso 1 1 calc R . .
C4 C 0.19227(7) 0.9410(3) 0.67995(13) 0.0256(3) Uani 1 1 d . . .
C5 C 0.24956(8) 0.9880(3) 0.75174(16) 0.0308(4) Uani 1 1 d . . .
H5 H 0.2556 0.9008 0.8258 0.037 Uiso 1 1 calc R . .
C6 C 0.12720(8) 0.7593(3) 0.70571(17) 0.0297(3) Uani 1 1 d . . .
H6A H 0.1362 0.6328 0.7741 0.036 Uiso 1 1 calc R . .
H6B H 0.1170 0.6279 0.6392 0.036 Uiso 1 1 calc R . .
C7 C 0.00881(8) 1.0146(4) 0.65276(17) 0.0305(4) Uani 1 1 d . . .
H7 H 0.0037 0.9308 0.5779 0.037 Uiso 1 1 calc R . .
C8 C 0.06368(7) 0.9536(3) 0.72879(14) 0.0260(3) Uani 1 1 d . . .
C9 C 0.05017(7) 1.1229(3) 0.82772(13) 0.0273(3) Uani 1 1 d . . .
H9 H 0.0784 1.1276 0.8957 0.033 Uiso 1 1 calc R . .
C10 C -0.01164(7) 1.2831(3) 0.80937(13) 0.0259(3) Uani 1 1 d . . .
C11 C -0.04624(8) 1.4930(4) 0.88304(17) 0.0319(4) Uani 1 1 d . . .
H11 H -0.0247 1.5331 0.9556 0.038 Uiso 1 1 calc R . .
N1 N 0.29583(7) 1.1766(3) 0.70109(11) 0.0296(3) Uani 1 1 d . . .
N2 N -0.03637(6) 1.2118(3) 0.70141(11) 0.0290(3) Uani 1 1 d . . .
O1 O 0.36084(6) 1.5877(3) 0.53858(11) 0.0390(3) Uani 1 1 d . . .
O2 O -0.10122(6) 1.6257(3) 0.86076(10) 0.0394(3) Uani 1 1 d . . .
H1N H 0.3355(11) 1.243(4) 0.7319(17) 0.040(5) Uiso 1 1 d . . .
H2N H -0.0747(10) 1.289(4) 0.6677(17) 0.035(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'
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
O1 C1 C2 126.12(18) . . ?
O1 C1 H1 116.9 . . ?
C2 C1 H1 116.9 . . ?
N1 C2 C3 107.52(13) . . ?
N1 C2 C1 123.47(14) . . ?
C3 C2 C1 128.99(15) . . ?
C2 C3 C4 107.95(13) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
C5 C4 C3 105.80(13) . . ?
C5 C4 C6 127.17(15) . . ?
C3 C4 C6 126.93(14) . . ?
N1 C5 C4 110.04(15) . . ?
N1 C5 H5 125.0 . . ?
C4 C5 H5 125.0 . . ?
C4 C6 C8 111.56(10) . . ?
C4 C6 H6A 109.3 . . ?
C8 C6 H6A 109.3 . . ?
C4 C6 H6B 109.3 . . ?
C8 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 C8 109.75(16) . . ?
N2 C7 H7 125.1 . . ?
C8 C7 H7 125.1 . . ?
C7 C8 C9 105.89(13) . . ?
C7 C8 C6 126.67(16) . . ?
C9 C8 C6 127.34(15) . . ?
C10 C9 C8 108.21(14) . . ?
C10 C9 H9 125.9 . . ?
C8 C9 H9 125.9 . . ?
N2 C10 C9 107.65(13) . . ?
N2 C10 C11 122.78(14) . . ?
C9 C10 C11 129.56(15) . . ?
O2 C11 C10 125.77(17) . . ?
O2 C11 H11 117.1 . . ?
C10 C11 H11 117.1 . . ?
C5 N1 C2 108.69(13) . . ?
C5 N1 H1N 126.0(13) . . ?
C2 N1 H1N 125.3(13) . . ?
C7 N2 C10 108.51(13) . . ?
C7 N2 H2N 125.9(12) . . ?
C10 N2 H2N 125.5(12) . . ?
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 O1 1.2310(18) . ?
C1 C2 1.427(2) . ?
C1 H1 0.9500 . ?
C2 N1 1.3711(19) . ?
C2 C3 1.393(2) . ?
C3 C4 1.408(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(2) . ?
C4 C6 1.508(2) . ?
C5 N1 1.353(2) . ?
C5 H5 0.9500 . ?
C6 C8 1.510(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.356(2) . ?
C7 C8 1.387(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(2) . ?
C9 C10 1.390(2) . ?
C9 H9 0.9500 . ?
C10 N2 1.3716(19) . ?
C10 C11 1.432(2) . ?
C11 O2 1.2262(18) . ?
C11 H11 0.9500 . ?
N1 H1N 0.88(2) . ?
N2 H2N 0.894(19) . ?
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
O1 C1 C2 N1 0.5(3) . . . . ?
O1 C1 C2 C3 178.60(16) . . . . ?
N1 C2 C3 C4 0.19(16) . . . . ?
C1 C2 C3 C4 -178.15(15) . . . . ?
C2 C3 C4 C5 -0.06(16) . . . . ?
C2 C3 C4 C6 176.44(14) . . . . ?
C3 C4 C5 N1 -0.10(17) . . . . ?
C6 C4 C5 N1 -176.58(14) . . . . ?
C5 C4 C6 C8 106.11(18) . . . . ?
C3 C4 C6 C8 -69.7(2) . . . . ?
N2 C7 C8 C9 0.15(18) . . . . ?
N2 C7 C8 C6 -176.28(14) . . . . ?
C4 C6 C8 C7 102.14(19) . . . . ?
C4 C6 C8 C9 -73.5(2) . . . . ?
C7 C8 C9 C10 -0.46(17) . . . . ?
C6 C8 C9 C10 175.93(14) . . . . ?
C8 C9 C10 N2 0.61(16) . . . . ?
C8 C9 C10 C11 -178.12(15) . . . . ?
N2 C10 C11 O2 1.7(3) . . . . ?
C9 C10 C11 O2 -179.75(16) . . . . ?
C4 C5 N1 C2 0.22(17) . . . . ?
C3 C2 N1 C5 -0.26(16) . . . . ?
C1 C2 N1 C5 178.20(14) . . . . ?
C8 C7 N2 C10 0.23(18) . . . . ?
C9 C10 N2 C7 -0.52(16) . . . . ?
C11 C10 N2 C7 178.32(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658807
