#------------------------------------------------------------------------------
#$Date: 2024-12-09 17:34:43 +0200 (Mon, 09 Dec 2024) $
#$Revision: 296805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/49/7154909.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_7154909
loop_
_publ_author_name
'Petersen, Anne Ugleholdt'
'Jevric, Martyn'
'Elm, Jonas'
'Olsen, Stine T.'
'Tortzen, Christian G.'
'Kadziola, Anders'
'Mikkelsen, Kurt V.'
'Nielsen, Mogens Brøndsted'
_publ_section_title
;
 Azulenium chemistry: towards new derivatives of photochromic
 dihydroazulenes.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2403
_journal_page_last               2412
_journal_paper_doi               10.1039/c5ob02523k
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C30 H20 N2'
_chemical_formula_weight         408.48
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-27
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-12-09 deposited with the CCDC.
2016-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.7675(11)
_cell_length_b                   9.1432(4)
_cell_length_c                   22.9483(13)
_cell_measurement_reflns_used    32052
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      24.57
_cell_measurement_theta_min      2.03
_cell_volume                     4357.5(4)
_computing_cell_refinement       'APEX2 v.2013.6-2, Bruker/Nonius'
_computing_data_collection       'APEX2 v.2013.6-2, Bruker/Nonius'
_computing_data_reduction        'APEX2 v.2013.6-2, Bruker/Nonius'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'APEX2 v.2013.6-2, Bruker/Nonius'
_diffrn_ambient_temperature      122(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32052
_diffrn_reflns_theta_full        24.57
_diffrn_reflns_theta_max         24.57
_diffrn_reflns_theta_min         2.03
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6831
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0396
_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)+(0.0373P)²+1.4625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                2675
_reflns_number_total             3648
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob02523k2.cif
_cod_data_source_block           mo_d8v847_0ma
_cod_depositor_comments
'Adding full bibliography for 7154909--7154911.cif.'
_cod_database_code               7154909
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'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
C30 C 0.18764(9) 0.7620(2) 0.49635(8) 0.0257(5) Uani 1 1 d .
H30 H 0.1915 0.7668 0.5376 0.031 Uiso 1 1 calc R
N2 N 0.24786(9) 1.00137(18) 0.09994(7) 0.0325(4) Uani 1 1 d .
N3 N 0.18830(8) 1.23821(16) 0.25244(7) 0.0245(4) Uani 1 1 d .
C1 C 0.16033(9) 0.6410(2) 0.47005(8) 0.0227(4) Uani 1 1 d .
H1 H 0.1460 0.5613 0.4933 0.027 Uiso 1 1 calc R
C2 C 0.15365(8) 0.63505(19) 0.41003(8) 0.0200(4) Uani 1 1 d .
H2 H 0.1344 0.5515 0.3926 0.024 Uiso 1 1 calc R
C3 C 0.17474(8) 0.74999(18) 0.37478(8) 0.0177(4) Uani 1 1 d .
C4 C 0.16543(8) 0.74539(19) 0.31028(8) 0.0184(4) Uani 1 1 d .
C5 C 0.15911(8) 0.87017(19) 0.27973(8) 0.0178(4) Uani 1 1 d .
H5 H 0.1543 0.9605 0.2997 0.021 Uiso 1 1 calc R
C6 C 0.15961(8) 0.86797(18) 0.21443(7) 0.0176(4) Uani 1 1 d .
H6 H 0.1969 0.8079 0.2008 0.021 Uiso 1 1 calc R
C7 C 0.16105(8) 1.02030(18) 0.18268(7) 0.0165(4) Uani 1 1 d .
C8 C 0.09362(8) 1.03667(18) 0.15499(7) 0.0162(4) Uani 1 1 d .
C9 C 0.07279(8) 1.17714(18) 0.12958(7) 0.0164(4) Uani 1 1 d .
C10 C 0.11712(9) 1.27661(18) 0.10607(7) 0.0192(4) Uani 1 1 d .
H10 H 0.1617 1.2535 0.1064 0.023 Uiso 1 1 calc R
C11 C 0.09680(9) 1.40805(19) 0.08239(8) 0.0213(4) Uani 1 1 d .
H11 H 0.1274 1.4741 0.0665 0.026 Uiso 1 1 calc R
C12 C 0.03196(9) 1.44348(19) 0.08185(8) 0.0237(4) Uani 1 1 d .
H12 H 0.0179 1.5327 0.0649 0.028 Uiso 1 1 calc R
C13 C 0.20406(9) 0.8693(2) 0.40179(8) 0.0230(4) Uani 1 1 d .
H13 H 0.2206 0.9468 0.3786 0.028 Uiso 1 1 calc R
C14 C 0.20949(9) 0.8767(2) 0.46171(8) 0.0259(5) Uani 1 1 d .
H14 H 0.2282 0.9605 0.4794 0.031 Uiso 1 1 calc R
C15 C 0.16261(9) 0.60210(19) 0.28251(8) 0.0212(4) Uani 1 1 d .
H15 H 0.1890 0.5277 0.2988 0.025 Uiso 1 1 calc R
C16 C 0.12642(9) 0.56443(19) 0.23610(8) 0.0239(5) Uani 1 1 d .
H16 H 0.1282 0.4647 0.2246 0.029 Uiso 1 1 calc R
C17 C 0.08546(9) 0.65799(18) 0.20193(8) 0.0225(4) Uani 1 1 d .
H17 H 0.0476 0.6173 0.1852 0.027 Uiso 1 1 calc R
C18 C 0.09817(9) 0.80029(18) 0.19255(7) 0.0176(4) Uani 1 1 d .
C19 C 0.06192(8) 0.90714(18) 0.15863(7) 0.0168(4) Uani 1 1 d .
C20 C 0.00238(8) 0.86411(17) 0.12757(7) 0.0166(4) Uani 1 1 d .
C21 C -0.05066(9) 0.80383(18) 0.15605(8) 0.0210(4) Uani 1 1 d .
H21 H -0.0509 0.7975 0.1974 0.025 Uiso 1 1 calc R
C22 C -0.10305(9) 0.75312(19) 0.12451(8) 0.0242(4) Uani 1 1 d .
H22 H -0.1393 0.7140 0.1443 0.029 Uiso 1 1 calc R
C23 C -0.10263(9) 0.75927(19) 0.06437(8) 0.0242(4) Uani 1 1 d .
H23 H -0.1382 0.7227 0.0428 0.029 Uiso 1 1 calc R
C24 C -0.05025(9) 0.81893(18) 0.03566(8) 0.0205(4) Uani 1 1 d .
H24 H -0.0500 0.8237 -0.0057 0.025 Uiso 1 1 calc R
C25 C 0.00147(9) 0.87130(18) 0.06674(7) 0.0191(4) Uani 1 1 d .
H25 H 0.0370 0.9129 0.0466 0.023 Uiso 1 1 calc R
C26 C -0.01206(9) 1.34822(19) 0.10620(8) 0.0250(5) Uani 1 1 d .
H26 H -0.0565 1.3732 0.1066 0.030 Uiso 1 1 calc R
C27 C 0.00792(9) 1.21654(19) 0.13002(8) 0.0217(4) Uani 1 1 d .
H27 H -0.0229 1.1524 0.1468 0.026 Uiso 1 1 calc R
C28 C 0.21061(9) 1.01336(19) 0.13635(8) 0.0200(4) Uani 1 1 d .
C29 C 0.17695(8) 1.14305(19) 0.22169(8) 0.0174(4) Uani 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
C1 C30 C14 119.18(17)
C1 C30 H30 120.4
C14 C30 H30 120.4
C30 C1 C2 120.44(17)
C30 C1 H1 119.8
C2 C1 H1 119.8
C1 C2 C3 120.99(17)
C1 C2 H2 119.5
C3 C2 H2 119.5
C13 C3 C2 117.91(16)
C13 C3 C4 121.26(16)
C2 C3 C4 120.82(16)
C5 C4 C15 122.02(16)
C5 C4 C3 120.35(16)
C15 C4 C3 117.63(15)
C4 C5 C6 120.59(16)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C18 109.47(14)
C5 C6 C7 116.84(14)
C18 C6 C7 103.05(13)
C5 C6 H6 109.1
C18 C6 H6 109.1
C7 C6 H6 109.1
C29 C7 C28 108.24(14)
C29 C7 C8 112.29(14)
C28 C7 C8 109.80(14)
C29 C7 C6 113.44(14)
C28 C7 C6 107.94(14)
C8 C7 C6 105.02(13)
C19 C8 C9 129.92(16)
C19 C8 C7 109.25(14)
C9 C8 C7 120.83(14)
C27 C9 C10 118.00(16)
C27 C9 C8 120.35(15)
C10 C9 C8 121.63(16)
C11 C10 C9 120.93(17)
C11 C10 H10 119.5
C9 C10 H10 119.5
C10 C11 C12 120.17(17)
C10 C11 H11 119.9
C12 C11 H11 119.9
C26 C12 C11 119.51(17)
C26 C12 H12 120.2
C11 C12 H12 120.2
C14 C13 C3 121.07(17)
C14 C13 H13 119.5
C3 C13 H13 119.5
C13 C14 C30 120.34(17)
C13 C14 H14 119.8
C30 C14 H14 119.8
C16 C15 C4 126.67(17)
C16 C15 H15 116.7
C4 C15 H15 116.7
C15 C16 C17 127.45(17)
C15 C16 H16 116.3
C17 C16 H16 116.3
C18 C17 C16 123.12(17)
C18 C17 H17 118.4
C16 C17 H17 118.4
C17 C18 C19 129.21(17)
C17 C18 C6 120.72(16)
C19 C18 C6 109.90(14)
C8 C19 C18 111.53(16)
C8 C19 C20 127.39(16)
C18 C19 C20 120.67(15)
C21 C20 C25 118.43(16)
C21 C20 C19 122.62(15)
C25 C20 C19 118.67(16)
C22 C21 C20 120.48(17)
C22 C21 H21 119.8
C20 C21 H21 119.8
C23 C22 C21 120.20(17)
C23 C22 H22 119.9
C21 C22 H22 119.9
C22 C23 C24 119.79(17)
C22 C23 H23 120.1
C24 C23 H23 120.1
C25 C24 C23 120.27(17)
C25 C24 H24 119.9
C23 C24 H24 119.9
C24 C25 C20 120.81(17)
C24 C25 H25 119.6
C20 C25 H25 119.6
C12 C26 C27 120.62(17)
C12 C26 H26 119.7
C27 C26 H26 119.7
C26 C27 C9 120.72(17)
C26 C27 H27 119.6
C9 C27 H27 119.6
N2 C28 C7 176.7(2)
N3 C29 C7 178.82(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C30 C1 1.382(3)
C30 C14 1.392(3)
C30 H30 0.9500
N2 C28 1.144(2)
N3 C29 1.145(2)
C1 C2 1.385(2)
C1 H1 0.9500
C2 C3 1.397(2)
C2 H2 0.9500
C3 C13 1.395(2)
C3 C4 1.493(2)
C4 C5 1.346(2)
C4 C15 1.458(2)
C5 C6 1.499(2)
C5 H5 0.9500
C6 C18 1.504(2)
C6 C7 1.572(2)
C6 H6 1.0000
C7 C29 1.473(2)
C7 C28 1.481(3)
C7 C8 1.545(2)
C8 C19 1.357(2)
C8 C9 1.475(2)
C9 C27 1.395(2)
C9 C10 1.402(2)
C10 C11 1.385(2)
C10 H10 0.9500
C11 C12 1.385(3)
C11 H11 0.9500
C12 C26 1.381(3)
C12 H12 0.9500
C13 C14 1.381(3)
C13 H13 0.9500
C14 H14 0.9500
C15 C16 1.348(3)
C15 H15 0.9500
C16 C17 1.439(2)
C16 H16 0.9500
C17 C18 1.345(2)
C17 H17 0.9500
C18 C19 1.458(2)
C19 C20 1.481(2)
C20 C21 1.394(2)
C20 C25 1.397(2)
C21 C22 1.387(3)
C21 H21 0.9500
C22 C23 1.381(3)
C22 H22 0.9500
C23 C24 1.384(3)
C23 H23 0.9500
C24 C25 1.375(2)
C24 H24 0.9500
C25 H25 0.9500
C26 C27 1.386(2)
C26 H26 0.9500
C27 H27 0.9500
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
C14 C30 C1 C2 -1.2(3)
C30 C1 C2 C3 0.6(3)
C1 C2 C3 C13 1.4(3)
C1 C2 C3 C4 -177.91(16)
C13 C3 C4 C5 -28.0(3)
C2 C3 C4 C5 151.35(17)
C13 C3 C4 C15 152.87(17)
C2 C3 C4 C15 -27.8(2)
C15 C4 C5 C6 -10.0(3)
C3 C4 C5 C6 170.85(15)
C4 C5 C6 C18 71.2(2)
C4 C5 C6 C7 -172.23(16)
C5 C6 C7 C29 13.6(2)
C18 C6 C7 C29 133.61(15)
C5 C6 C7 C28 133.48(16)
C18 C6 C7 C28 -106.46(16)
C5 C6 C7 C8 -109.42(16)
C18 C6 C7 C8 10.64(16)
C29 C7 C8 C19 -134.39(15)
C28 C7 C8 C19 105.14(17)
C6 C7 C8 C19 -10.68(18)
C29 C7 C8 C9 46.0(2)
C28 C7 C8 C9 -74.46(19)
C6 C7 C8 C9 169.72(14)
C19 C8 C9 C27 31.0(3)
C7 C8 C9 C27 -149.54(16)
C19 C8 C9 C10 -151.05(18)
C7 C8 C9 C10 28.5(2)
C27 C9 C10 C11 -1.9(2)
C8 C9 C10 C11 -179.98(16)
C9 C10 C11 C12 0.3(3)
C10 C11 C12 C26 1.4(3)
C2 C3 C13 C14 -2.9(3)
C4 C3 C13 C14 176.50(17)
C3 C13 C14 C30 2.3(3)
C1 C30 C14 C13 -0.2(3)
C5 C4 C15 C16 -33.7(3)
C3 C4 C15 C16 145.47(19)
C4 C15 C16 C17 3.6(3)
C15 C16 C17 C18 32.2(3)
C16 C17 C18 C19 179.16(17)
C16 C17 C18 C6 4.3(3)
C5 C6 C18 C17 -66.8(2)
C7 C6 C18 C17 168.16(16)
C5 C6 C18 C19 117.37(15)
C7 C6 C18 C19 -7.63(18)
C9 C8 C19 C18 -174.30(16)
C7 C8 C19 C18 6.2(2)
C9 C8 C19 C20 13.2(3)
C7 C8 C19 C20 -166.40(16)
C17 C18 C19 C8 -174.14(18)
C6 C18 C19 C8 1.2(2)
C17 C18 C19 C20 -1.0(3)
C6 C18 C19 C20 174.31(15)
C8 C19 C20 C21 -129.90(19)
C18 C19 C20 C21 58.2(2)
C8 C19 C20 C25 56.3(2)
C18 C19 C20 C25 -115.66(18)
C25 C20 C21 C22 -0.3(2)
C19 C20 C21 C22 -174.16(16)
C20 C21 C22 C23 1.3(3)
C21 C22 C23 C24 -1.3(3)
C22 C23 C24 C25 0.4(3)
C23 C24 C25 C20 0.6(3)
C21 C20 C25 C24 -0.6(2)
C19 C20 C25 C24 173.49(15)
C11 C12 C26 C27 -1.3(3)
C12 C26 C27 C9 -0.4(3)
C10 C9 C27 C26 2.0(3)
C8 C9 C27 C26 -179.95(16)
C29 C7 C28 N2 165(3)
C8 C7 C28 N2 -72(4)
C6 C7 C28 N2 42(4)
C28 C7 C29 N3 169(100)
C8 C7 C29 N3 48(10)
C6 C7 C29 N3 -71(10)
