#------------------------------------------------------------------------------
#$Date: 2019-11-10 06:19:38 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225701 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/55/4515544.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_4515544
loop_
_publ_author_name
'Noto, Naoki'
'Tanaka, Yuya'
'Koike, Takashi'
'Akita, Munetaka'
_publ_section_title
;
 Strongly Reducing (Diarylamino)anthracene Catalyst for Metal-Free
 Visible-Light Photocatalytic Fluoroalkylation
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              9408
_journal_paper_doi               10.1021/acscatal.8b02885
_journal_volume                  8
_journal_year                    2018
_chemical_formula_sum            'C54 H60 N2'
_chemical_formula_weight         737.04
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                100.111(2)
_cell_angle_beta                 103.430(3)
_cell_angle_gamma                98.334(2)
_cell_formula_units_Z            1
_cell_length_a                   8.3369(16)
_cell_length_b                   9.3962(18)
_cell_length_c                   14.592(3)
_cell_measurement_reflns_used    2331
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.571
_cell_measurement_theta_min      2.245
_cell_volume                     1073.8(4)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5092
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.470
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_description       tip
_exptl_crystal_F_000             398
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.380
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.380
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0486
_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)+(0.0652P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2844
_reflns_number_total             3707
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b02885_si_002.cif
_cod_data_source_block           N1763_0m
_cod_database_code               4515544
_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_min   0.993
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2013-2
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
C1 C 0.0532(2) 0.1085(2) 0.58590(13) 0.0164(4) Uani 1 1 d . .
C2 C -0.0361(2) 0.1436(2) 0.50139(13) 0.0167(4) Uani 1 1 d . .
C3 C -0.0793(2) 0.2845(2) 0.50034(14) 0.0198(4) Uani 1 1 d . .
H3 H -0.0435 0.3593 0.5578 0.024 Uiso 1 1 calc R U
C4 C -0.1715(2) 0.3135(2) 0.41775(14) 0.0238(5) Uani 1 1 d . .
H4 H -0.2008 0.4076 0.4183 0.029 Uiso 1 1 calc R U
C5 C -0.2235(2) 0.2034(2) 0.33114(14) 0.0236(5) Uani 1 1 d . .
H5 H -0.2869 0.2248 0.2739 0.028 Uiso 1 1 calc R U
C6 C -0.1841(2) 0.0686(2) 0.32893(14) 0.0206(4) Uani 1 1 d . .
H6 H -0.2197 -0.0034 0.2701 0.025 Uiso 1 1 calc R U
C7 C -0.0895(2) 0.0328(2) 0.41396(13) 0.0169(4) Uani 1 1 d . .
C8 C 0.0104(2) 0.21179(19) 0.74137(13) 0.0167(4) Uani 1 1 d . .
C9 C 0.0833(2) 0.2460(2) 0.84110(13) 0.0197(4) Uani 1 1 d . .
H9 H 0.2021 0.2704 0.8653 0.024 Uiso 1 1 calc R U
C10 C -0.0160(2) 0.2446(2) 0.90421(13) 0.0211(4) Uani 1 1 d . .
H10 H 0.0365 0.2702 0.9716 0.025 Uiso 1 1 calc R U
C11 C -0.1912(2) 0.2068(2) 0.87295(13) 0.0180(4) Uani 1 1 d . .
C12 C -0.2610(2) 0.1656(2) 0.77376(13) 0.0205(4) Uani 1 1 d . .
H12 H -0.3794 0.1350 0.7495 0.025 Uiso 1 1 calc R U
C13 C -0.1627(2) 0.1679(2) 0.70924(14) 0.0204(4) Uani 1 1 d . .
H13 H -0.2148 0.1388 0.6419 0.024 Uiso 1 1 calc R U
C14 C -0.2973(2) 0.2194(2) 0.94545(13) 0.0216(5) Uani 1 1 d . .
C15 C -0.4812(3) 0.1490(2) 0.89898(15) 0.0293(5) Uani 1 1 d . .
H15A H -0.5269 0.1977 0.8473 0.044 Uiso 1 1 calc R U
H15B H -0.5445 0.1599 0.9477 0.044 Uiso 1 1 calc R U
H15C H -0.4906 0.0441 0.8719 0.044 Uiso 1 1 calc R U
C16 C -0.2863(3) 0.3842(2) 0.98597(16) 0.0354(6) Uani 1 1 d . .
H16A H -0.1689 0.4308 1.0182 0.053 Uiso 1 1 calc R U
H16B H -0.3541 0.3952 1.0325 0.053 Uiso 1 1 calc R U
H16C H -0.3289 0.4316 0.9330 0.053 Uiso 1 1 calc R U
C17 C -0.2315(3) 0.1440(3) 1.02779(16) 0.0368(6) Uani 1 1 d . .
H17A H -0.2342 0.0401 1.0012 0.055 Uiso 1 1 calc R U
H17B H -0.3025 0.1508 1.0727 0.055 Uiso 1 1 calc R U
H17C H -0.1157 0.1929 1.0621 0.055 Uiso 1 1 calc R U
C18 C 0.2566(2) 0.32308(19) 0.68909(13) 0.0162(4) Uani 1 1 d . .
C19 C 0.3671(2) 0.2999(2) 0.63163(13) 0.0193(4) Uani 1 1 d . .
H19 H 0.3433 0.2120 0.5833 0.023 Uiso 1 1 calc R U
C20 C 0.5105(2) 0.4036(2) 0.64435(14) 0.0215(4) Uani 1 1 d . .
H20 H 0.5821 0.3855 0.6034 0.026 Uiso 1 1 calc R U
C21 C 0.5543(2) 0.5337(2) 0.71496(13) 0.0182(4) Uani 1 1 d . .
C22 C 0.4434(2) 0.5545(2) 0.77166(13) 0.0190(4) Uani 1 1 d . .
H22 H 0.4693 0.6409 0.8215 0.023 Uiso 1 1 calc R U
C23 C 0.2960(2) 0.45384(19) 0.75816(13) 0.0177(4) Uani 1 1 d . .
H23 H 0.2212 0.4747 0.7967 0.021 Uiso 1 1 calc R U
C24 C 0.7148(2) 0.6458(2) 0.72645(14) 0.0218(5) Uani 1 1 d . .
C25 C 0.7072(3) 0.6958(3) 0.63091(16) 0.0364(6) Uani 1 1 d . .
H25A H 0.6080 0.7403 0.6141 0.055 Uiso 1 1 calc R U
H25B H 0.7000 0.6106 0.5796 0.055 Uiso 1 1 calc R U
H25C H 0.8088 0.7686 0.6382 0.055 Uiso 1 1 calc R U
C26 C 0.8683(3) 0.5728(2) 0.75073(16) 0.0278(5) Uani 1 1 d . .
H26A H 0.9708 0.6439 0.7571 0.042 Uiso 1 1 calc R U
H26B H 0.8578 0.4873 0.6989 0.042 Uiso 1 1 calc R U
H26C H 0.8742 0.5408 0.8116 0.042 Uiso 1 1 calc R U
C27 C 0.7376(3) 0.7810(2) 0.80639(16) 0.0288(5) Uani 1 1 d . .
H27A H 0.7446 0.7509 0.8679 0.043 Uiso 1 1 calc R U
H27B H 0.6416 0.8300 0.7917 0.043 Uiso 1 1 calc R U
H27C H 0.8413 0.8493 0.8110 0.043 Uiso 1 1 calc R U
N1 N 0.10793(19) 0.21756(16) 0.67407(10) 0.0175(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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C7 121.28(17) . 2_556
C2 C1 N1 119.89(16) . .
C7 C1 N1 118.83(16) 2_556 .
C1 C2 C3 122.20(17) . .
C1 C2 C7 118.94(17) . .
C3 C2 C7 118.83(17) . .
C4 C3 C2 120.82(18) . .
C4 C3 H3 119.6 . .
C2 C3 H3 119.6 . .
C3 C4 C5 120.09(18) . .
C3 C4 H4 120.0 . .
C5 C4 H4 120.0 . .
C6 C5 C4 120.92(18) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
C5 C6 C7 120.87(18) . .
C5 C6 H6 119.6 . .
C7 C6 H6 119.6 . .
C1 C7 C6 121.73(18) 2_556 .
C1 C7 C2 119.78(16) 2_556 .
C6 C7 C2 118.45(17) . .
C13 C8 C9 117.75(17) . .
C13 C8 N1 120.07(16) . .
C9 C8 N1 122.17(17) . .
C10 C9 C8 120.44(18) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C9 C10 C11 122.42(18) . .
C9 C10 H10 118.8 . .
C11 C10 H10 118.8 . .
C12 C11 C10 116.36(17) . .
C12 C11 C14 122.93(17) . .
C10 C11 C14 120.63(17) . .
C13 C12 C11 121.84(18) . .
C13 C12 H12 119.1 . .
C11 C12 H12 119.1 . .
C8 C13 C12 121.04(17) . .
C8 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
C15 C14 C11 112.15(16) . .
C15 C14 C17 108.05(16) . .
C11 C14 C17 110.50(17) . .
C15 C14 C16 108.28(17) . .
C11 C14 C16 107.91(15) . .
C17 C14 C16 109.92(17) . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C14 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C14 C17 H17A 109.5 . .
C14 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C14 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C23 C18 C19 117.53(17) . .
C23 C18 N1 122.18(16) . .
C19 C18 N1 120.26(16) . .
C20 C19 C18 120.70(18) . .
C20 C19 H19 119.7 . .
C18 C19 H19 119.7 . .
C19 C20 C21 122.57(18) . .
C19 C20 H20 118.7 . .
C21 C20 H20 118.7 . .
C22 C21 C20 115.92(17) . .
C22 C21 C24 123.25(17) . .
C20 C21 C24 120.81(17) . .
C21 C22 C23 122.41(18) . .
C21 C22 H22 118.8 . .
C23 C22 H22 118.8 . .
C18 C23 C22 120.80(17) . .
C18 C23 H23 119.6 . .
C22 C23 H23 119.6 . .
C27 C24 C21 112.42(17) . .
C27 C24 C26 108.23(16) . .
C21 C24 C26 109.36(15) . .
C27 C24 C25 108.63(17) . .
C21 C24 C25 109.18(16) . .
C26 C24 C25 108.95(18) . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C24 C26 H26A 109.5 . .
C24 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C24 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C24 C27 H27A 109.5 . .
C24 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C24 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C8 N1 C18 124.27(15) . .
C8 N1 C1 117.55(15) . .
C18 N1 C1 118.18(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.404(3) .
C1 C7 1.405(3) 2_556
C1 N1 1.429(2) .
C2 C3 1.423(3) .
C2 C7 1.430(3) .
C3 C4 1.365(3) .
C3 H3 0.9500 .
C4 C5 1.418(3) .
C4 H4 0.9500 .
C5 C6 1.351(3) .
C5 H5 0.9500 .
C6 C7 1.429(3) .
C6 H6 0.9500 .
C7 C1 1.405(3) 2_556
C8 C13 1.385(3) .
C8 C9 1.399(3) .
C8 N1 1.416(2) .
C9 C10 1.374(3) .
C9 H9 0.9500 .
C10 C11 1.397(3) .
C10 H10 0.9500 .
C11 C12 1.389(3) .
C11 C14 1.529(3) .
C12 C13 1.385(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.521(3) .
C14 C17 1.534(3) .
C14 C16 1.539(3) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 C23 1.388(3) .
C18 C19 1.397(3) .
C18 N1 1.417(2) .
C19 C20 1.382(3) .
C19 H19 0.9500 .
C20 C21 1.394(3) .
C20 H20 0.9500 .
C21 C22 1.389(3) .
C21 C24 1.534(3) .
C22 C23 1.389(3) .
C22 H22 0.9500 .
C23 H23 0.9500 .
C24 C27 1.523(3) .
C24 C26 1.537(3) .
C24 C25 1.539(3) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
