#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:54:50 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267086 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/98/1559823.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_1559823
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         'C20 H14 N4'
_chemical_formula_sum            'C20 H14 N4'
_chemical_formula_weight         310.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-02 deposited with the CCDC.	2020-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.900(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8604(11)
_cell_length_b                   11.0803(8)
_cell_length_c                   9.0716(6)
_cell_measurement_reflns_used    4764
_cell_measurement_temperature    185(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.73
_cell_volume                     1499.03(18)
_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      185.01
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0405
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11365
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         2.732
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1595 before and 0.0782 after correction.
The Ratio of minimum to maximum transmission is 0.9380.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0393
_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)+(0.0493P)²+0.9304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1269
_reflns_number_total             1528
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc06017h2.cif
_cod_data_source_block           mo_h19040201_0m_a
_cod_depositor_comments
;Adding full bibliography for 1559823--1559829.cif.

 Adding full bibliography for 1559823--1559829.cif.
;
_cod_database_code               1559823
_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   0.985
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C3(H3), C7(H7), C5(H5), C1(H1), C2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.25039(7) 0.40246(10) 0.71358(13) 0.0267(3) Uani 1 1 d . . . . .
N1 N 0.16528(8) 0.35079(12) 0.85386(15) 0.0370(3) Uani 1 1 d . . . . .
C6 C 0.43003(8) 0.50475(11) 0.56316(14) 0.0228(3) Uani 1 1 d . . . . .
C8 C 0.53892(8) 0.60899(11) 0.47393(14) 0.0232(3) Uani 1 1 d . . . . .
C9 C 0.57984(9) 0.71641(12) 0.44388(15) 0.0268(3) Uani 1 1 d . . . . .
H9 H 0.559697 0.792444 0.467177 0.032 Uiso 1 1 calc R . . . .
C10 C 0.64696(9) 0.71256(12) 0.38272(15) 0.0272(3) Uani 1 1 d . . . . .
H10 H 0.673328 0.785224 0.363622 0.033 Uiso 1 1 calc R . . . .
C3 C 0.18160(9) 0.48487(13) 0.67886(17) 0.0321(3) Uani 1 1 d . . . . .
H3 H 0.171859 0.551466 0.609086 0.038 Uiso 1 1 calc R . . . .
C7 C 0.46992(9) 0.61122(11) 0.53705(15) 0.0245(3) Uani 1 1 d . . . . .
H7 H 0.449792 0.686516 0.562664 0.029 Uiso 1 1 calc R . . . .
C4 C 0.32241(9) 0.40106(12) 0.65262(15) 0.0251(3) Uani 1 1 d . . . . .
C5 C 0.35975(8) 0.50608(12) 0.62814(14) 0.0247(3) Uani 1 1 d . . . . .
H5 H 0.339015 0.580743 0.654373 0.030 Uiso 1 1 calc R . . . .
C1 C 0.23719(9) 0.32450(13) 0.81940(16) 0.0318(3) Uani 1 1 d . . . . .
H1 H 0.275660 0.258411 0.863495 0.038 Uiso 1 1 calc R . . . .
C2 C 0.13052(10) 0.45109(14) 0.76520(19) 0.0381(4) Uani 1 1 d . . . . .
H2 H 0.077569 0.491603 0.764374 0.046 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
C3 N2 C4 126.54(11) . . ?
C1 N2 C3 106.43(11) . . ?
C1 N2 C4 127.02(12) . . ?
C1 N1 C2 104.37(12) . . ?
C7 C6 C8 119.41(12) . 5_666 ?
C7 C6 C5 121.59(12) . . ?
C5 C6 C8 118.99(11) . 5_666 ?
C9 C8 C6 118.28(12) . 5_666 ?
C7 C8 C6 119.40(11) . 5_666 ?
C7 C8 C9 122.32(11) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.53(12) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C4 119.63(12) . 5_666 ?
C4 C10 H10 120.2 5_666 . ?
N2 C3 H3 127.2 . . ?
C2 C3 N2 105.53(13) . . ?
C2 C3 H3 127.2 . . ?
C6 C7 C8 121.18(11) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C10 C4 N2 118.40(11) 5_666 . ?
C5 C4 N2 120.32(11) . . ?
C5 C4 C10 121.29(12) . 5_666 ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.27(12) . . ?
C4 C5 H5 119.9 . . ?
N2 C1 H1 123.8 . . ?
N1 C1 N2 112.46(13) . . ?
N1 C1 H1 123.8 . . ?
N1 C2 H2 124.4 . . ?
C3 C2 N1 111.21(13) . . ?
C3 C2 H2 124.4 . . ?
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 C3 1.3746(18) . ?
N2 C4 1.4285(16) . ?
N2 C1 1.3595(17) . ?
N1 C1 1.3138(18) . ?
N1 C2 1.373(2) . ?
C6 C8 1.4342(17) 5_666 ?
C6 C7 1.3965(18) . ?
C6 C5 1.4275(17) . ?
C8 C9 1.4257(17) . ?
C8 C7 1.3973(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3583(18) . ?
C10 H10 0.9500 . ?
C10 C4 1.4248(18) 5_666 ?
C3 H3 0.9500 . ?
C3 C2 1.3572(19) . ?
C7 H7 0.9500 . ?
C4 C5 1.3578(18) . ?
C5 H5 0.9500 . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
