#------------------------------------------------------------------------------
#$Date: 2022-02-09 23:58:18 +0100 (Wed 09 de Feb de 2022) $
#$Revision: 272891 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/97/7129701.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_7129701
loop_
_publ_author_name
'Wang, Danfeng'
'Huang, Hai'
'Zhu, Xiaolin'
_publ_section_title
;
 Development of Anthrazoline Photocatalyst for Promoting Amination and
 Amidation Reactions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07315J
_journal_year                    2022
_chemical_formula_moiety         'C50 H32 N2'
_chemical_formula_sum            'C50 H32 N2'
_chemical_formula_weight         660.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-11 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.118(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.501(6)
_cell_length_b                   21.209(9)
_cell_length_c                   13.563(6)
_cell_measurement_reflns_used    8874
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      31.32
_cell_measurement_theta_min      2.29
_cell_volume                     3560(3)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.984
_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  0.0334
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            93709
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.731
_diffrn_reflns_theta_min         1.795
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9608
_exptl_absorpt_correction_T_min  0.8571
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0871 before and 0.0485 after correction.
The Ratio of minimum to maximum transmission is 0.8921.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         7437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0588P)²+1.8747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1250
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5978
_reflns_number_total             7437
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc07315j2.cif
_cod_data_source_block           zx12a_zxl_5b_0m
_cod_database_code               7129701
_shelx_shelxl_version_number     2017/1
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20), C29(H29)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C17(H17), C18(H18), C23(H23), C25(H25), C27(H27),
 C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36),
  C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44),
 C45(H45), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.78069(9) 0.16549(6) 0.97504(9) 0.0203(3) Uani 1 1 d . . . . .
N2 N 1.00024(9) 0.20636(6) 1.29758(9) 0.0196(3) Uani 1 1 d . . . . .
C3 C 0.81660(11) 0.27730(7) 1.02842(11) 0.0181(3) Uani 1 1 d . . . . .
C4 C 1.04057(11) 0.24819(7) 1.36641(11) 0.0186(3) Uani 1 1 d . . . . .
C5 C 0.97653(11) 0.34245(7) 1.27063(11) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.72036(11) 0.18897(7) 0.89362(11) 0.0205(3) Uani 1 1 d . . . . .
C7 C 0.83061(11) 0.20995(7) 1.04416(11) 0.0184(3) Uani 1 1 d . . . . .
C8 C 0.73597(11) 0.36905(7) 0.91641(11) 0.0206(3) Uani 1 1 d . . . . .
C9 C 0.94262(11) 0.23114(7) 1.20886(11) 0.0184(3) Uani 1 1 d . . . . .
C10 C 0.96164(11) 0.41230(7) 1.25521(11) 0.0189(3) Uani 1 1 d . . . . .
C11 C 0.89437(11) 0.18880(7) 1.13355(11) 0.0192(3) Uani 1 1 d . . . . .
H11 H 0.904953 0.145713 1.143199 0.023 Uiso 1 1 calc R . . . .
C12 C 0.92848(11) 0.29838(7) 1.19258(11) 0.0177(3) Uani 1 1 d . . . . .
C13 C 0.65159(11) 0.15269(7) 0.81276(11) 0.0218(3) Uani 1 1 d . . . . .
C14 C 0.75174(11) 0.29998(7) 0.93623(11) 0.0187(3) Uani 1 1 d . . . . .
C15 C 0.86606(11) 0.31911(7) 1.10263(11) 0.0188(3) Uani 1 1 d . . . . .
H15 H 0.857287 0.362233 1.091995 0.023 Uiso 1 1 calc R . . . .
C16 C 1.03199(11) 0.31634(7) 1.35701(11) 0.0182(3) Uani 1 1 d . . . . .
C17 C 0.90910(12) 0.44790(7) 1.32234(11) 0.0221(3) Uani 1 1 d . . . . .
H17 H 0.884862 0.428384 1.376472 0.026 Uiso 1 1 calc R . . . .
C18 C 0.63364(12) 0.08760(7) 0.80091(12) 0.0246(3) Uani 1 1 d . . . . .
H18 H 0.669628 0.058932 0.845761 0.029 Uiso 1 1 calc R . . . .
C19 C 0.70502(11) 0.25523(7) 0.86950(11) 0.0206(3) Uani 1 1 d . . . . .
C20 C 1.09111(11) 0.34792(7) 1.45329(11) 0.0194(3) Uani 1 1 d . . . . .
H20 H 1.039108 0.372316 1.485428 0.023 Uiso 1 1 calc R . . . .
C21 C 1.12993(11) 0.29056(7) 1.51888(11) 0.0201(3) Uani 1 1 d . . . . .
C22 C 1.18635(12) 0.39049(7) 1.43611(11) 0.0213(3) Uani 1 1 d . . . . .
C23 C 0.98227(12) 0.50793(7) 1.15778(12) 0.0266(3) Uani 1 1 d . . . . .
H23 H 1.005952 0.527635 1.103546 0.032 Uiso 1 1 calc R . . . .
C24 C 1.10248(11) 0.23358(7) 1.46729(11) 0.0198(3) Uani 1 1 d . . . . .
C25 C 0.89374(13) 0.51302(7) 1.30667(12) 0.0272(3) Uani 1 1 d . . . . .
H25 H 0.858648 0.536412 1.350456 0.033 Uiso 1 1 calc R . . . .
C26 C 0.59592(12) 0.19587(7) 0.74310(11) 0.0230(3) Uani 1 1 d . . . . .
C27 C 0.93085(13) 0.54322(7) 1.22548(13) 0.0274(3) Uani 1 1 d . . . . .
H27 H 0.921423 0.586443 1.216574 0.033 Uiso 1 1 calc R . . . .
C28 C 0.52041(12) 0.17488(8) 0.66227(12) 0.0265(3) Uani 1 1 d . . . . .
H28 H 0.483145 0.203469 0.618087 0.032 Uiso 1 1 calc R . . . .
C29 C 0.62713(12) 0.26422(7) 0.77058(11) 0.0230(3) Uani 1 1 d . . . . .
H29 H 0.666883 0.282206 0.719954 0.028 Uiso 1 1 calc R . . . .
C30 C 0.77442(13) 0.39668(8) 0.83341(13) 0.0309(4) Uani 1 1 d . . . . .
H30 H 0.810559 0.372006 0.792008 0.037 Uiso 1 1 calc R . . . .
C31 C 0.99751(12) 0.44315(7) 1.17252(12) 0.0236(3) Uani 1 1 d . . . . .
H31 H 1.031499 0.419888 1.127778 0.028 Uiso 1 1 calc R . . . .
C32 C 0.50325(13) 0.11009(8) 0.65053(12) 0.0287(4) Uani 1 1 d . . . . .
H32 H 0.454596 0.095266 0.597365 0.034 Uiso 1 1 calc R . . . .
C33 C 0.55907(13) 0.06669(8) 0.71863(12) 0.0275(3) Uani 1 1 d . . . . .
H33 H 0.546686 0.023720 0.709311 0.033 Uiso 1 1 calc R . . . .
C34 C 0.68222(14) 0.40648(8) 0.97975(14) 0.0318(4) Uani 1 1 d . . . . .
H34 H 0.657506 0.388714 1.035018 0.038 Uiso 1 1 calc R . . . .
C35 C 1.13397(12) 0.17539(7) 1.51282(12) 0.0240(3) Uani 1 1 d . . . . .
H35 H 1.115851 0.137593 1.479891 0.029 Uiso 1 1 calc R . . . .
C36 C 1.18965(12) 0.29051(8) 1.61606(12) 0.0246(3) Uani 1 1 d . . . . .
H36 H 1.207273 0.328244 1.649347 0.029 Uiso 1 1 calc R . . . .
C37 C 0.53016(12) 0.30595(7) 0.78211(13) 0.0276(4) Uani 1 1 d . . . . .
C38 C 0.75858(14) 0.46053(9) 0.81320(16) 0.0410(5) Uani 1 1 d . . . . .
H38 H 0.784074 0.478626 0.758558 0.049 Uiso 1 1 calc R . . . .
C39 C 1.18229(14) 0.45592(8) 1.44967(12) 0.0275(3) Uani 1 1 d . . . . .
H39 H 1.119121 0.474465 1.464634 0.033 Uiso 1 1 calc R . . . .
C40 C 0.70450(15) 0.49701(9) 0.87510(19) 0.0474(5) Uani 1 1 d . . . . .
H40 H 0.693223 0.539622 0.861142 0.057 Uiso 1 1 calc R . . . .
C41 C 1.22171(12) 0.23260(8) 1.66117(12) 0.0279(4) Uani 1 1 d . . . . .
H41 H 1.261181 0.231844 1.724644 0.033 Uiso 1 1 calc R . . . .
C42 C 0.47043(13) 0.29534(9) 0.86186(14) 0.0367(4) Uani 1 1 d . . . . .
H42 H 0.489004 0.262304 0.906062 0.044 Uiso 1 1 calc R . . . .
C43 C 1.36674(15) 0.46623(10) 1.41632(14) 0.0406(5) Uani 1 1 d . . . . .
H43 H 1.426766 0.491166 1.410664 0.049 Uiso 1 1 calc R . . . .
C44 C 1.37079(14) 0.40132(9) 1.40022(14) 0.0369(4) Uani 1 1 d . . . . .
H44 H 1.432965 0.383132 1.382342 0.044 Uiso 1 1 calc R . . . .
C45 C 1.19410(12) 0.17569(8) 1.61030(12) 0.0274(3) Uani 1 1 d . . . . .
H45 H 1.215505 0.137605 1.640886 0.033 Uiso 1 1 calc R . . . .
C46 C 1.28150(13) 0.36368(8) 1.41097(12) 0.0288(4) Uani 1 1 d . . . . .
H46 H 1.285140 0.320363 1.401349 0.035 Uiso 1 1 calc R . . . .
C47 C 0.49989(15) 0.35527(8) 0.71373(16) 0.0407(5) Uani 1 1 d . . . . .
H47 H 0.538865 0.361746 0.661064 0.049 Uiso 1 1 calc R . . . .
C48 C 1.27253(16) 0.49369(9) 1.44091(13) 0.0377(4) Uani 1 1 d . . . . .
H48 H 1.269612 0.536947 1.451459 0.045 Uiso 1 1 calc R . . . .
C49 C 0.66637(16) 0.47058(9) 0.95877(17) 0.0446(5) Uani 1 1 d . . . . .
H49 H 0.630740 0.495715 0.999959 0.053 Uiso 1 1 calc R . . . .
C50 C 0.41290(16) 0.39415(9) 0.72402(19) 0.0503(6) Uani 1 1 d . . . . .
H50 H 0.392411 0.425984 0.678065 0.060 Uiso 1 1 calc R . . . .
C51 C 0.38330(15) 0.33474(11) 0.87397(17) 0.0524(6) Uani 1 1 d . . . . .
H51 H 0.343827 0.328314 0.926309 0.063 Uiso 1 1 calc R . . . .
C52 C 0.35621(16) 0.38447(10) 0.8054(2) 0.0597(7) Uani 1 1 d . . . . .
H52 H 0.299642 0.411395 0.814323 0.072 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
C6 N1 C7 116.29(12) . . ?
C4 N2 C9 116.43(12) . . ?
C7 C3 C14 119.16(12) . . ?
C15 C3 C7 118.70(13) . . ?
C15 C3 C14 122.14(13) . . ?
N2 C4 C16 125.73(13) . . ?
N2 C4 C24 126.43(13) . . ?
C16 C4 C24 107.84(12) . . ?
C12 C5 C10 119.63(12) . . ?
C16 C5 C10 123.16(13) . . ?
C16 C5 C12 117.18(13) . . ?
N1 C6 C13 127.32(14) . . ?
N1 C6 C19 125.92(13) . . ?
C19 C6 C13 106.70(13) . . ?
N1 C7 C3 121.81(13) . . ?
N1 C7 C11 119.75(13) . . ?
C11 C7 C3 118.43(12) . . ?
C30 C8 C14 119.87(14) . . ?
C34 C8 C14 120.27(14) . . ?
C34 C8 C30 119.85(15) . . ?
N2 C9 C11 119.20(13) . . ?
N2 C9 C12 122.13(12) . . ?
C11 C9 C12 118.65(13) . . ?
C17 C10 C5 119.73(13) . . ?
C17 C10 C31 119.23(14) . . ?
C31 C10 C5 121.02(13) . . ?
C7 C11 C9 122.63(13) . . ?
C9 C12 C5 119.03(13) . . ?
C15 C12 C5 122.58(13) . . ?
C15 C12 C9 118.36(12) . . ?
C18 C13 C6 130.65(14) . . ?
C18 C13 C26 120.05(14) . . ?
C26 C13 C6 109.24(13) . . ?
C3 C14 C8 121.00(12) . . ?
C19 C14 C3 117.57(13) . . ?
C19 C14 C8 121.43(13) . . ?
C3 C15 C12 123.21(13) . . ?
C4 C16 C20 109.49(12) . . ?
C5 C16 C4 119.48(13) . . ?
C5 C16 C20 131.03(13) . . ?
C25 C17 C10 119.53(14) . . ?
C13 C18 C33 118.27(15) . . ?
C6 C19 C29 111.13(12) . . ?
C14 C19 C6 119.19(13) . . ?
C14 C19 C29 129.50(14) . . ?
C21 C20 C16 102.55(12) . . ?
C22 C20 C16 114.28(12) . . ?
C22 C20 C21 111.27(12) . . ?
C24 C21 C20 110.71(13) . . ?
C24 C21 C36 121.17(14) . . ?
C36 C21 C20 128.06(13) . . ?
C39 C22 C20 121.21(14) . . ?
C39 C22 C46 118.73(14) . . ?
C46 C22 C20 119.99(14) . . ?
C31 C23 C27 119.66(15) . . ?
C21 C24 C4 109.35(12) . . ?
C35 C24 C4 130.80(13) . . ?
C35 C24 C21 119.85(14) . . ?
C17 C25 C27 120.79(15) . . ?
C13 C26 C29 111.27(13) . . ?
C28 C26 C13 121.47(14) . . ?
C28 C26 C29 127.24(14) . . ?
C25 C27 C23 119.96(14) . . ?
C32 C28 C26 118.24(15) . . ?
C26 C29 C19 101.58(12) . . ?
C37 C29 C19 113.10(13) . . ?
C37 C29 C26 113.24(12) . . ?
C38 C30 C8 120.41(17) . . ?
C23 C31 C10 120.82(14) . . ?
C28 C32 C33 120.78(14) . . ?
C32 C33 C18 121.19(15) . . ?
C49 C34 C8 119.37(16) . . ?
C24 C35 C45 118.68(14) . . ?
C41 C36 C21 119.02(14) . . ?
C42 C37 C29 119.86(15) . . ?
C47 C37 C29 120.31(16) . . ?
C47 C37 C42 119.83(16) . . ?
C40 C38 C30 119.50(17) . . ?
C22 C39 C48 120.67(16) . . ?
C38 C40 C49 121.04(17) . . ?
C36 C41 C45 120.03(14) . . ?
C51 C42 C37 119.8(2) . . ?
C48 C43 C44 119.96(16) . . ?
C43 C44 C46 120.01(17) . . ?
C41 C45 C35 121.24(14) . . ?
C44 C46 C22 120.74(16) . . ?
C50 C47 C37 121.0(2) . . ?
C43 C48 C39 119.86(17) . . ?
C34 C49 C40 119.81(18) . . ?
C47 C50 C52 118.7(2) . . ?
C42 C51 C52 119.0(2) . . ?
C50 C52 C51 121.56(18) . . ?
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
N1 C6 1.342(2) . ?
N1 C7 1.4115(19) . ?
N2 C4 1.3342(19) . ?
N2 C9 1.4136(19) . ?
C3 C7 1.451(2) . ?
C3 C14 1.472(2) . ?
C3 C15 1.416(2) . ?
C4 C16 1.454(2) . ?
C4 C24 1.506(2) . ?
C5 C10 1.504(2) . ?
C5 C12 1.475(2) . ?
C5 C16 1.389(2) . ?
C6 C13 1.506(2) . ?
C6 C19 1.449(2) . ?
C7 C11 1.426(2) . ?
C8 C14 1.497(2) . ?
C8 C30 1.412(2) . ?
C8 C34 1.408(2) . ?
C9 C11 1.428(2) . ?
C9 C12 1.450(2) . ?
C10 C17 1.414(2) . ?
C10 C31 1.424(2) . ?
C12 C15 1.422(2) . ?
C13 C18 1.404(2) . ?
C13 C26 1.425(2) . ?
C14 C19 1.383(2) . ?
C16 C20 1.558(2) . ?
C17 C25 1.407(2) . ?
C18 C33 1.420(2) . ?
C19 C29 1.554(2) . ?
C20 C21 1.544(2) . ?
C20 C22 1.538(2) . ?
C21 C24 1.414(2) . ?
C21 C36 1.420(2) . ?
C22 C39 1.402(2) . ?
C22 C46 1.403(2) . ?
C23 C27 1.408(2) . ?
C23 C31 1.398(2) . ?
C24 C35 1.411(2) . ?
C25 C27 1.408(2) . ?
C26 C28 1.414(2) . ?
C26 C29 1.533(2) . ?
C28 C32 1.396(2) . ?
C29 C37 1.527(2) . ?
C30 C38 1.390(3) . ?
C32 C33 1.416(2) . ?
C34 C49 1.397(2) . ?
C35 C45 1.426(2) . ?
C36 C41 1.405(2) . ?
C37 C42 1.416(3) . ?
C37 C47 1.414(3) . ?
C38 C40 1.386(3) . ?
C39 C48 1.402(2) . ?
C40 C49 1.408(3) . ?
C41 C45 1.409(2) . ?
C42 C51 1.401(3) . ?
C43 C44 1.396(3) . ?
C43 C48 1.396(3) . ?
C44 C46 1.397(2) . ?
C47 C50 1.387(3) . ?
C50 C52 1.409(4) . ?
C51 C52 1.415(4) . ?
