#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:54:50 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267086 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/98/1559829.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_1559829
loop_
_publ_author_name
'Bai, Sha'
'Ma, Li-Li'
'Yang, Tao'
'Wang, Fang'
'Wang, Li-Feng'
'Hahn, F. Ekkehardt'
'Wang, Yao-Yu'
'Han, Ying-Feng'
_publ_section_title
;
 Supramolecular-induced regiocontrol over the photochemical [4 + 4]
 cyclodimerization of NHC- or azole-substituted anthracenes.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2165
_journal_page_last               2171
_journal_paper_doi               10.1039/d0sc06017h
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C28 H18 N4'
_chemical_formula_sum            'C28 H18 N4'
_chemical_formula_weight         410.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-24 deposited with the CCDC.	2020-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                69.264(5)
_cell_angle_beta                 78.354(5)
_cell_angle_gamma                79.800(6)
_cell_formula_units_Z            1
_cell_length_a                   6.4661(11)
_cell_length_b                   8.1703(13)
_cell_length_c                   10.3854(17)
_cell_measurement_reflns_used    4245
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      26.70
_cell_measurement_theta_min      2.68
_cell_volume                     499.20(14)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      179.98
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5617
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.697
_diffrn_reflns_theta_min         2.818
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1301 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.9011.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       block
_exptl_crystal_F_000             214
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2082
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0463P)²+0.4098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1903
_reflns_number_total             2082
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc06017h2.cif
_cod_data_source_block           mo_h2019121501_0m_a
_cod_depositor_comments
;Adding full bibliography for 1559823--1559829.cif.

 Adding full bibliography for 1559823--1559829.cif.
;
_cod_database_code               1559829
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C1, N2, C8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C11(H11), C9(H9), C1(H1), C4(H4), C6(H6), C3(H3), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 1.1561(3) 0.5877(2) 0.16214(16) 0.0330(4) Uani 1 1 d . U . . .
N1 N 1.4758(3) 0.4555(2) 0.2062(2) 0.0418(5) Uani 1 1 d . . . . .
C10 C 0.6612(3) 0.8942(2) 0.07676(19) 0.0279(4) Uani 1 1 d . . . . .
C13 C 0.1295(3) 1.1517(2) 0.13603(19) 0.0303(4) Uani 1 1 d . . . . .
H13 H 0.110248 1.128094 0.233803 0.036 Uiso 1 1 calc R . . . .
C8 C 0.9949(3) 0.7070(2) 0.0850(2) 0.0299(4) Uani 1 1 d . U . . .
C14 C -0.0212(3) 1.2596(2) 0.0615(2) 0.0311(4) Uani 1 1 d . . . . .
H14 H -0.143299 1.312577 0.106505 0.037 Uiso 1 1 calc R . . . .
C12 C 0.3166(3) 1.0728(2) 0.07029(18) 0.0273(4) Uani 1 1 d . . . . .
C11 C 0.4785(3) 0.9683(2) 0.14342(19) 0.0298(4) Uani 1 1 d . . . . .
H11 H 0.464320 0.947096 0.240664 0.036 Uiso 1 1 calc R . . . .
C9 C 0.8229(3) 0.7823(2) 0.15159(19) 0.0305(4) Uani 1 1 d . . . . .
H9 H 0.810530 0.760110 0.248858 0.037 Uiso 1 1 calc R . . . .
C2 C 1.3244(3) 0.3735(3) 0.3146(2) 0.0336(4) Uani 1 1 d . . . . .
C7 C 1.1193(3) 0.4546(2) 0.2899(2) 0.0308(4) Uani 1 1 d . . . . .
C1 C 1.3577(3) 0.5807(3) 0.1219(2) 0.0374(4) Uani 1 1 d . U . . .
H1 H 1.418588 0.660354 0.036809 0.045 Uiso 1 1 calc R . . . .
C4 C 1.1720(4) 0.1639(3) 0.5202(2) 0.0405(5) Uani 1 1 d . . . . .
H4 H 1.186812 0.062692 0.600319 0.049 Uiso 1 1 calc R . . . .
C6 C 0.9369(3) 0.3930(3) 0.3786(2) 0.0367(5) Uani 1 1 d . . . . .
H6 H 0.798650 0.448463 0.360731 0.044 Uiso 1 1 calc R . . . .
C3 C 1.3505(4) 0.2260(3) 0.4326(2) 0.0393(5) Uani 1 1 d . . . . .
H3 H 1.488246 0.170330 0.451555 0.047 Uiso 1 1 calc R . . . .
C5 C 0.9686(4) 0.2459(3) 0.4946(2) 0.0409(5) Uani 1 1 d . . . . .
H5 H 0.848650 0.199637 0.558464 0.049 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
_geom_angle_publ_flag
C7 N2 C8 126.07(17) . . ?
C1 N2 C8 126.03(17) . . ?
C1 N2 C7 107.82(16) . . ?
C1 N1 C2 102.43(17) . . ?
C11 C10 C12 119.31(17) . 2_675 ?
C11 C10 C9 121.69(17) . . ?
C9 C10 C12 118.97(17) . 2_675 ?
C14 C13 H13 119.3 . . ?
C14 C13 C12 121.31(17) . . ?
C12 C13 H13 119.3 . . ?
C14 C8 N2 118.19(17) 2_675 . ?
C9 C8 N2 120.44(17) . . ?
C9 C8 C14 121.37(17) . 2_675 ?
C13 C14 C8 119.56(17) . 2_675 ?
C13 C14 H14 120.2 . . ?
C8 C14 H14 120.2 2_675 . ?
C13 C12 C10 118.34(16) . 2_675 ?
C11 C12 C10 119.23(17) . 2_675 ?
C11 C12 C13 122.42(17) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.46(17) . . ?
C12 C11 H11 119.3 . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.42(17) . . ?
C8 C9 H9 119.8 . . ?
N1 C2 C7 110.49(17) . . ?
N1 C2 C3 129.61(19) . . ?
C3 C2 C7 119.83(19) . . ?
N2 C7 C2 103.33(17) . . ?
C6 C7 N2 133.99(18) . . ?
C6 C7 C2 122.56(18) . . ?
N2 C1 N1 115.92(19) . . ?
N2 C1 H1 122.0 . . ?
N1 C1 H1 122.0 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.60(19) . . ?
C5 C4 H4 119.2 . . ?
C7 C6 H6 121.9 . . ?
C5 C6 C7 116.12(19) . . ?
C5 C6 H6 121.9 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.07(19) . . ?
C4 C3 H3 121.0 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
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
N2 C8 1.450(2) . ?
N2 C7 1.394(2) . ?
N2 C1 1.284(3) . ?
N1 C2 1.388(3) . ?
N1 C1 1.324(3) . ?
C10 C12 1.435(3) 2_675 ?
C10 C11 1.398(3) . ?
C10 C9 1.421(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.358(3) . ?
C13 C12 1.431(3) . ?
C8 C14 1.426(3) 2_675 ?
C8 C9 1.358(3) . ?
C14 H14 0.9500 . ?
C12 C11 1.395(3) . ?
C11 H11 0.9500 . ?
C9 H9 0.9500 . ?
C2 C7 1.403(3) . ?
C2 C3 1.396(3) . ?
C7 C6 1.392(3) . ?
C1 H1 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.369(3) . ?
C4 C5 1.397(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.388(3) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
