#------------------------------------------------------------------------------
#$Date: 2021-11-04 03:43:30 +0200 (Thu, 04 Nov 2021) $
#$Revision: 270290 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565115.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_1565115
loop_
_publ_author_name
'Wu, Ni'
'Xiao, Hui'
'Lou, Yuheng'
'Han, Mingxi'
'Guo, Zhiyong'
'Zhan, Hongbing'
_publ_section_title
;
 Manipulating the Position of Triplet Chromophores To Achieve a Dynamic
 Photoactivated Ultralong Organic Phosphorescence Effect
;
_journal_issue                   41
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              22848
_journal_page_last               22855
_journal_paper_doi               10.1021/acs.jpcc.1c06860
_journal_volume                  125
_journal_year                    2021
_chemical_formula_moiety         'C30 H19 Cl N2'
_chemical_formula_sum            'C30 H19 Cl N2'
_chemical_formula_weight         442.92
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 93.110(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6705(15)
_cell_length_b                   13.9677(12)
_cell_length_c                   9.4774(8)
_cell_measurement_reflns_used    3627
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.250
_cell_measurement_theta_min      1.903
_cell_volume                     2203.5(3)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6374
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         1.903
_exptl_absorpt_coefficient_mu    0.195
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.198
_refine_ls_abs_structure_details
;
 Flack x determined using 974 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_coef       0.038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3627
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0576
_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)+(0.0839P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1611
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.826
_reflns_Friedel_fraction_max     0.827
_reflns_number_gt                2584
_reflns_number_total             3627
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp1c06860_si_003.cif
_cod_data_source_block           cc
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1565115
_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.
;
_shelxl_version_number           2014-1
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'
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
Cl1 Cl 0.70008(13) 0.94568(12) 0.64199(18) 0.0539(6) Uani 1 1 d . . . . .
N1 N 0.8302(4) 1.2836(4) 0.9538(6) 0.0456(14) Uani 1 1 d . . . . .
N2 N 0.8654(3) 0.9602(4) 0.7809(6) 0.0413(14) Uani 1 1 d . . . . .
C1 C 0.8449(4) 1.1198(4) 0.8719(7) 0.0399(16) Uani 1 1 d . . . . .
H1 H 0.8967 1.1184 0.9136 0.080 Uiso 1 1 calc R U . . .
C2 C 0.7978(4) 1.2010(5) 0.8849(7) 0.0411(17) Uani 1 1 d . . . . .
C3 C 0.7191(4) 1.2007(5) 0.8289(7) 0.0454(17) Uani 1 1 d . . . . .
H3 H 0.6872 1.2547 0.8384 0.080 Uiso 1 1 calc R U . . .
C4 C 0.6875(4) 1.1207(5) 0.7586(8) 0.0452(17) Uani 1 1 d . . . . .
H4 H 0.6343 1.1203 0.7235 0.080 Uiso 1 1 calc R U . . .
C5 C 0.7361(4) 1.0420(5) 0.7416(7) 0.0414(17) Uani 1 1 d . . . . .
C6 C 0.8154(4) 1.0410(5) 0.7975(7) 0.0373(15) Uani 1 1 d . . . . .
C7 C 0.9057(5) 1.3230(5) 0.9309(7) 0.0454(17) Uani 1 1 d . . . . .
C8 C 0.9617(5) 1.2948(6) 0.8355(9) 0.056(2) Uani 1 1 d . . . . .
H8 H 0.9525 1.2426 0.7757 0.080 Uiso 1 1 calc R U . . .
C9 C 1.0315(6) 1.3481(6) 0.8336(10) 0.070(2) Uani 1 1 d . . . . .
H9 H 1.0706 1.3307 0.7721 0.080 Uiso 1 1 calc R U . . .
C10 C 1.0447(6) 1.4263(7) 0.9205(11) 0.075(3) Uani 1 1 d . . . . .
H10 H 1.0925 1.4603 0.9165 0.080 Uiso 1 1 calc R U . . .
C11 C 0.9889(6) 1.4550(6) 1.0125(9) 0.067(2) Uani 1 1 d . . . . .
H11 H 0.9985 1.5079 1.0707 0.080 Uiso 1 1 calc R U . . .
C12 C 0.9174(5) 1.4035(5) 1.0175(7) 0.0505(19) Uani 1 1 d . . . . .
C13 C 0.8454(5) 1.4146(5) 1.0951(8) 0.0518(19) Uani 1 1 d . . . . .
C14 C 0.8232(7) 1.4804(6) 1.1954(9) 0.069(3) Uani 1 1 d . . . . .
H14 H 0.8575 1.5301 1.2236 0.080 Uiso 1 1 calc R U . . .
C15 C 0.7498(7) 1.4707(6) 1.2521(9) 0.074(3) Uani 1 1 d . . . . .
H15 H 0.7337 1.5157 1.3172 0.080 Uiso 1 1 calc R U . . .
C16 C 0.6993(6) 1.3956(7) 1.2146(9) 0.071(3) Uani 1 1 d . . . . .
H16 H 0.6506 1.3896 1.2571 0.080 Uiso 1 1 calc R U . . .
C17 C 0.7201(5) 1.3290(6) 1.1144(8) 0.056(2) Uani 1 1 d . . . . .
H17 H 0.6860 1.2787 1.0877 0.080 Uiso 1 1 calc R U . . .
C18 C 0.7937(5) 1.3404(5) 1.0559(7) 0.0478(18) Uani 1 1 d . . . . .
C19 C 0.9343(4) 0.9581(5) 0.7028(7) 0.0419(17) Uani 1 1 d . . . . .
C20 C 0.9651(4) 1.0293(5) 0.6192(7) 0.0485(19) Uani 1 1 d . . . . .
H20 H 0.9417 1.0896 0.6117 0.080 Uiso 1 1 calc R U . . .
C21 C 1.0328(5) 1.0057(8) 0.5472(9) 0.068(2) Uani 1 1 d . . . . .
H21 H 1.0553 1.0516 0.4902 0.080 Uiso 1 1 calc R U . . .
C22 C 1.0676(5) 0.9162(8) 0.5578(10) 0.074(3) Uani 1 1 d . . . . .
H22 H 1.1130 0.9031 0.5083 0.080 Uiso 1 1 calc R U . . .
C23 C 1.0365(5) 0.8466(7) 0.6396(9) 0.067(2) Uani 1 1 d . . . . .
H23 H 1.0604 0.7865 0.6455 0.080 Uiso 1 1 calc R U . . .
C24 C 0.9684(5) 0.8665(5) 0.7147(7) 0.0475(18) Uani 1 1 d . . . . .
C25 C 0.9204(5) 0.8117(5) 0.8079(7) 0.0492(18) Uani 1 1 d . . . . .
C26 C 0.9265(6) 0.7196(5) 0.8646(9) 0.067(2) Uani 1 1 d . . . . .
H26 H 0.9685 0.6795 0.8425 0.080 Uiso 1 1 calc R U . . .
C27 C 0.8692(7) 0.6895(6) 0.9537(10) 0.077(3) Uani 1 1 d . . . . .
H27 H 0.8725 0.6281 0.9915 0.080 Uiso 1 1 calc R U . . .
C28 C 0.8072(6) 0.7484(6) 0.9878(9) 0.069(3) Uani 1 1 d . . . . .
H28 H 0.7697 0.7260 1.0491 0.080 Uiso 1 1 calc R U . . .
C29 C 0.7988(5) 0.8397(5) 0.9340(7) 0.054(2) Uani 1 1 d . . . . .
H29 H 0.7561 0.8788 0.9563 0.080 Uiso 1 1 calc R U . . .
C30 C 0.8567(5) 0.8707(5) 0.8453(7) 0.0445(17) 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'
Cl Cl 0.1484 0.1585 '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 N1 C18 108.0(6) . . ?
C7 N1 C2 124.8(6) . . ?
C18 N1 C2 127.2(6) . . ?
C19 N2 C30 108.6(5) . . ?
C19 N2 C6 125.5(5) . . ?
C30 N2 C6 125.9(5) . . ?
C6 C1 C2 120.5(7) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 119.4(6) . . ?
C3 C2 N1 120.5(6) . . ?
C1 C2 N1 120.1(6) . . ?
C2 C3 C4 120.7(6) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.1(7) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.9(6) . . ?
C4 C5 Cl1 119.6(6) . . ?
C6 C5 Cl1 119.4(5) . . ?
C1 C6 C5 119.2(6) . . ?
C1 C6 N2 119.7(6) . . ?
C5 C6 N2 121.1(6) . . ?
C8 C7 C12 122.1(7) . . ?
C8 C7 N1 129.0(7) . . ?
C12 C7 N1 108.8(6) . . ?
C9 C8 C7 116.8(7) . . ?
C9 C8 H8 121.6 . . ?
C7 C8 H8 121.6 . . ?
C10 C9 C8 121.7(9) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C11 C10 C9 121.4(9) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 118.8(8) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C7 119.1(8) . . ?
C11 C12 C13 134.0(7) . . ?
C7 C12 C13 106.9(6) . . ?
C14 C13 C18 119.6(8) . . ?
C14 C13 C12 132.7(8) . . ?
C18 C13 C12 107.7(6) . . ?
C15 C14 C13 118.8(9) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 121.3(8) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 121.0(9) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 117.2(8) . . ?
C18 C17 H17 121.4 . . ?
C16 C17 H17 121.4 . . ?
C17 C18 C13 122.1(7) . . ?
C17 C18 N1 129.3(7) . . ?
C13 C18 N1 108.6(6) . . ?
C20 C19 N2 128.8(6) . . ?
C20 C19 C24 122.6(6) . . ?
N2 C19 C24 108.5(6) . . ?
C19 C20 C21 116.5(8) . . ?
C19 C20 H20 121.7 . . ?
C21 C20 H20 121.7 . . ?
C22 C21 C20 121.9(8) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C23 C22 C21 121.1(8) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 119.4(8) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C23 C24 C19 118.5(7) . . ?
C23 C24 C25 134.2(7) . . ?
C19 C24 C25 107.3(6) . . ?
C26 C25 C30 118.9(8) . . ?
C26 C25 C24 133.9(7) . . ?
C30 C25 C24 107.1(6) . . ?
C27 C26 C25 118.8(8) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C28 C27 C26 121.1(8) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C27 C28 C29 122.0(8) . . ?
C27 C28 H28 119.0 . . ?
C29 C28 H28 119.0 . . ?
C28 C29 C30 117.0(8) . . ?
C28 C29 H29 121.5 . . ?
C30 C29 H29 121.5 . . ?
C29 C30 N2 129.5(6) . . ?
C29 C30 C25 122.1(7) . . ?
N2 C30 C25 108.4(6) . . ?
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
Cl1 C5 1.732(7) . ?
N1 C7 1.402(9) . ?
N1 C18 1.414(9) . ?
N1 C2 1.418(9) . ?
N2 C19 1.400(8) . ?
N2 C30 1.402(8) . ?
N2 C6 1.417(8) . ?
C1 C6 1.384(9) . ?
C1 C2 1.389(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(10) . ?
C3 C4 1.390(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(10) . ?
C7 C8 1.391(10) . ?
C7 C12 1.400(10) . ?
C8 C9 1.382(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(13) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.450(11) . ?
C13 C14 1.386(11) . ?
C13 C18 1.387(10) . ?
C14 C15 1.369(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(14) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(11) . ?
C17 H17 0.9300 . ?
C19 C20 1.388(10) . ?
C19 C24 1.402(10) . ?
C20 C21 1.389(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(13) . ?
C21 H21 0.9300 . ?
C22 C23 1.363(13) . ?
C22 H22 0.9300 . ?
C23 C24 1.401(10) . ?
C23 H23 0.9300 . ?
C24 C25 1.443(10) . ?
C25 C26 1.394(10) . ?
C25 C30 1.405(10) . ?
C26 C27 1.375(13) . ?
C26 H26 0.9300 . ?
C27 C28 1.374(13) . ?
C27 H27 0.9300 . ?
C28 C29 1.378(11) . ?
C28 H28 0.9300 . ?
C29 C30 1.383(10) . ?
C29 H29 0.9300 . ?
