#------------------------------------------------------------------------------
#$Date: 2019-11-23 22:41:55 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235400 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/69/4036910.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_4036910
loop_
_publ_author_name
'García-Iriepa, Cristina'
'Ernst, Hanna A.'
'Liang, Yu'
'Unterreiner, Andreas-Neil'
'Frutos, Luis Manuel'
'Sampedro, Diego'
_publ_section_title
;
 Study of Model Systems for Bilirubin and Bilin Chromophores:
 Determination and Modification of Thermal and Photochemical Properties.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6292
_journal_page_last               6302
_journal_paper_doi               10.1021/acs.joc.6b00892
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C13 H14 N2 O1'
_chemical_formula_sum            'C13 H14 N2 O'
_chemical_formula_weight         214.26
_chemical_name_common            CG-12
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 106.78(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.598(5)
_cell_length_b                   7.254(5)
_cell_length_c                   17.992(14)
_cell_measurement_reflns_used    4889
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0.0
_cell_volume                     2324(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4877
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         4.33
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.0533
_exptl_absorpt_correction_T_min  0.8951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0505
_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)+(0.0556P)²+1.3086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1253
_reflns_number_gt                1721
_reflns_number_total             2541
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo6b00892_si_002.cif
_cod_data_source_block           import
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C13 H14 N2 O1'
_cod_database_code               4036910
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O1 O 0.17204(7) -0.20712(18) -0.08155(8) 0.0472(4) Uani 1 1 d .
N1 N 0.21396(8) -0.0193(2) 0.02619(8) 0.0331(4) Uani 1 1 d .
N2 N 0.40060(9) 0.0854(2) 0.31897(9) 0.0427(4) Uani 1 1 d .
C1 C 0.16678(9) -0.0671(2) -0.04476(10) 0.0338(4) Uani 1 1 d .
C2 C 0.10924(9) 0.0792(2) -0.06771(10) 0.0308(4) Uani 1 1 d .
C3 C 0.12500(9) 0.2075(2) -0.01148(10) 0.0303(4) Uani 1 1 d .
C4 C 0.19209(9) 0.1483(2) 0.05064(10) 0.0300(4) Uani 1 1 d .
C5 C 0.22222(10) 0.2388(2) 0.11760(10) 0.0339(4) Uani 1 1 d .
H5 H 0.1995 0.3507 0.1223 0.041 Uiso 1 1 calc R
C6 C 0.28522(9) 0.1877(2) 0.18402(10) 0.0309(4) Uani 1 1 d .
C7 C 0.28923(11) 0.2576(3) 0.25721(11) 0.0431(5) Uani 1 1 d .
H7 H 0.2531 0.3406 0.2630 0.052 Uiso 1 1 calc R
C8 C 0.34654(12) 0.2041(3) 0.32104(11) 0.0474(5) Uani 1 1 d .
H8 H 0.3475 0.2543 0.3689 0.057 Uiso 1 1 calc R
C9 C 0.39711(9) 0.0212(3) 0.24852(11) 0.0375(4) Uani 1 1 d .
H9 H 0.4341 -0.0615 0.2447 0.045 Uiso 1 1 calc R
C10 C 0.34295(9) 0.0678(2) 0.18094(10) 0.0324(4) Uani 1 1 d .
H10 H 0.3449 0.0198 0.1336 0.039 Uiso 1 1 calc R
C11 C 0.08411(10) 0.3835(3) -0.00789(11) 0.0391(5) Uani 1 1 d .
H11A H 0.0406 0.3915 -0.0522 0.059 Uiso 1 1 calc R
H11B H 0.1167 0.4861 -0.0080 0.059 Uiso 1 1 calc R
H11C H 0.0689 0.3856 0.0387 0.059 Uiso 1 1 calc R
C12 C 0.04588(9) 0.0646(3) -0.14064(10) 0.0364(4) Uani 1 1 d .
H12A H 0.0654 0.0280 -0.1829 0.044 Uiso 1 1 calc R
H12B H 0.0224 0.1844 -0.1532 0.044 Uiso 1 1 calc R
C13 C -0.01265(11) -0.0747(3) -0.13286(13) 0.0546(6) Uani 1 1 d .
H13A H -0.0330 -0.0370 -0.0919 0.082 Uiso 1 1 calc R
H13B H 0.0104 -0.1937 -0.1209 0.082 Uiso 1 1 calc R
H13C H -0.0522 -0.0812 -0.1808 0.082 Uiso 1 1 calc R
H1 H 0.2500(11) -0.094(3) 0.0493(12) 0.047(6) 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
C1 N1 C4 110.40(15)
C1 N1 H1 119.0(14)
C4 N1 H1 130.5(14)
C8 N2 C9 114.96(16)
O1 C1 N1 125.53(16)
O1 C1 C2 127.24(16)
N1 C1 C2 107.23(15)
C3 C2 C1 107.68(15)
C3 C2 C12 131.04(16)
C1 C2 C12 121.23(15)
C2 C3 C4 108.77(14)
C2 C3 C11 128.32(16)
C4 C3 C11 122.91(16)
C5 C4 N1 128.68(16)
C5 C4 C3 125.36(16)
N1 C4 C3 105.91(15)
C4 C5 C6 129.67(16)
C4 C5 H5 115.2
C6 C5 H5 115.2
C7 C6 C10 115.64(16)
C7 C6 C5 119.52(16)
C10 C6 C5 124.82(16)
C8 C7 C6 120.17(18)
C8 C7 H7 119.9
C6 C7 H7 119.9
N2 C8 C7 124.56(18)
N2 C8 H8 117.7
C7 C8 H8 117.7
N2 C9 C10 125.09(17)
N2 C9 H9 117.5
C10 C9 H9 117.5
C9 C10 C6 119.53(16)
C9 C10 H10 120.2
C6 C10 H10 120.2
C3 C11 H11A 109.5
C3 C11 H11B 109.5
H11A C11 H11B 109.5
C3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C2 C12 C13 111.75(15)
C2 C12 H12A 109.3
C13 C12 H12A 109.3
C2 C12 H12B 109.3
C13 C12 H12B 109.3
H12A C12 H12B 107.9
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.232(2)
N1 C1 1.369(2)
N1 C4 1.393(2)
N1 H1 0.87(2)
N2 C8 1.332(2)
N2 C9 1.335(2)
C1 C2 1.479(2)
C2 C3 1.343(2)
C2 C12 1.493(2)
C3 C4 1.478(2)
C3 C11 1.497(2)
C4 C5 1.344(2)
C5 C6 1.459(2)
C5 H5 0.9300
C6 C7 1.393(2)
C6 C10 1.395(2)
C7 C8 1.378(3)
C7 H7 0.9300
C8 H8 0.9300
C9 C10 1.379(2)
C9 H9 0.9300
C10 H10 0.9300
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 C13 1.521(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
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
C4 N1 C1 O1 179.48(17)
C4 N1 C1 C2 -0.84(18)
O1 C1 C2 C3 -179.09(18)
N1 C1 C2 C3 1.24(18)
O1 C1 C2 C12 3.3(3)
N1 C1 C2 C12 -176.39(15)
C1 C2 C3 C4 -1.13(18)
C12 C2 C3 C4 176.18(16)
C1 C2 C3 C11 179.15(16)
C12 C2 C3 C11 -3.6(3)
C1 N1 C4 C5 177.75(17)
C1 N1 C4 C3 0.17(18)
C2 C3 C4 C5 -177.04(16)
C11 C3 C4 C5 2.7(3)
C2 C3 C4 N1 0.64(18)
C11 C3 C4 N1 -179.62(15)
N1 C4 C5 C6 -0.9(3)
C3 C4 C5 C6 176.19(16)
C4 C5 C6 C7 -154.67(19)
C4 C5 C6 C10 23.9(3)
C10 C6 C7 C8 -1.6(3)
C5 C6 C7 C8 177.08(18)
C9 N2 C8 C7 1.4(3)
C6 C7 C8 N2 -0.4(3)
C8 N2 C9 C10 -0.4(3)
N2 C9 C10 C6 -1.6(3)
C7 C6 C10 C9 2.5(2)
C5 C6 C10 C9 -176.08(16)
C3 C2 C12 C13 -102.7(2)
C1 C2 C12 C13 74.3(2)
