#------------------------------------------------------------------------------
#$Date: 2020-06-03 01:21:17 +0300 (Wed, 03 Jun 2020) $
#$Revision: 252540 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/35/4003563.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_4003563
loop_
_publ_author_name
'Liu, Kun'
'Lei, Yilong'
'Fu, Hongbing'
_publ_section_title
;
 A General Synthetic Strategy to a Library of Luminescent All-Organic
 Core--Shell Microstructures
;
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.0c01184
_journal_year                    2020
_chemical_formula_sum            'C19 H9 N5 O'
_chemical_formula_weight         323.31
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                106.69(3)
_cell_angle_beta                 100.39(3)
_cell_angle_gamma                100.56(3)
_cell_formula_units_Z            1
_cell_length_a                   6.7349(13)
_cell_length_b                   7.8881(16)
_cell_length_c                   7.8913(16)
_cell_measurement_reflns_used    1240
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8545
_cell_measurement_theta_min      3.1756
_cell_volume                     382.49(17)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3572
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         3.176
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             166
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     676
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1431P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1748
_refine_ls_wR_factor_ref         0.1898
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1883
_reflns_number_total             2434
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm0c01184_si_010.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        382.50(15)
_cod_database_code               4003563
_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_min   0.982
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'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
N1 N 0.7506(11) 0.4920(10) 0.6315(9) 0.0422(18) Uani 1 1 d . . . . .
N2 N 0.7565(11) 0.8033(9) 0.3163(9) 0.0388(17) Uani 1 1 d . . . . .
N3 N 0.4346(10) 0.0339(8) -0.4491(8) 0.0351(16) Uani 1 1 d . . . . .
N4 N 0.4386(10) -0.2770(9) -0.1412(9) 0.0395(17) Uani 1 1 d . . . . .
O1A O 0.018(5) -0.113(3) 0.101(3) 0.069(8) Uani 0.25 1 d D U P A 1
O1B O 0.129(4) 0.621(3) 0.077(3) 0.064(7) Uani 0.25 1 d D U P A 1
C1 C 0.034(3) 0.002(3) 0.014(3) 0.044(3) Uani 0.5 1 d D U P A 1
C2 C -0.022(3) -0.030(3) -0.171(3) 0.032(3) Uani 0.5 1 d . U P A 1
C3 C -0.003(3) 0.110(3) -0.248(3) 0.038(3) Uani 0.5 1 d . U P A 1
C4 C 0.054(2) 0.286(2) -0.145(2) 0.038(2) Uani 0.25 1 d . U P A 1
N1B N 0.054(2) 0.286(2) -0.145(2) 0.038(2) Uani 0.25 1 d . U P A 1
C5 C 0.099(5) 0.327(3) 0.054(3) 0.029(3) Uani 0.5 1 d D U P A 1
C6 C 0.088(5) 0.189(4) 0.130(4) 0.036(3) Uani 0.5 1 d . U P A 1
C7 C 0.130(2) 0.219(2) 0.311(2) 0.041(2) Uani 0.25 1 d . U P A 1
N1A N 0.130(2) 0.219(2) 0.311(2) 0.041(2) Uani 0.25 1 d . U P A 1
C8 C 0.191(3) 0.397(3) 0.420(3) 0.041(3) Uani 0.5 1 d . U P A 1
C9 C 0.200(4) 0.560(3) 0.351(3) 0.043(4) Uani 0.5 1 d D U P A 1
C10 C 0.164(3) 0.511(2) 0.164(2) 0.038(3) Uani 0.5 1 d D U P A 1
O1C O 0.075(3) 0.299(2) -0.261(2) 0.050(5) Uani 0.25 1 d D U P B 2
O1D O 0.188(3) 0.276(3) 0.472(2) 0.047(5) Uani 0.25 1 d D U P B 2
C1' C 0.061(2) 0.046(2) 0.139(2) 0.040(2) Uani 0.25 1 d . U P B 2
N1D N 0.061(2) 0.046(2) 0.139(2) 0.040(2) Uani 0.25 1 d . U P B 2
C2' C -0.004(3) -0.067(3) -0.059(3) 0.041(3) Uani 0.5 1 d . U P B 2
C3' C -0.007(3) 0.016(3) -0.212(3) 0.042(4) Uani 0.5 1 d D U P B 2
C4' C 0.023(3) 0.193(2) -0.166(2) 0.037(3) Uani 0.5 1 d D U P B 2
C5' C 0.093(5) 0.300(3) 0.022(2) 0.029(3) Uani 0.5 1 d D U P B 2
C6' C 0.104(5) 0.221(4) 0.161(3) 0.035(3) Uani 0.5 1 d D U P B 2
C7' C 0.150(3) 0.337(2) 0.341(2) 0.043(3) Uani 0.5 1 d D U P B 2
C8' C 0.218(4) 0.524(2) 0.377(3) 0.039(4) Uani 0.5 1 d D U P B 2
C9' C 0.189(3) 0.598(3) 0.235(3) 0.042(3) Uani 0.5 1 d . U P B 2
C10' C 0.136(2) 0.496(2) 0.073(2) 0.036(3) Uani 0.25 1 d . U P B 2
N1C N 0.136(2) 0.496(2) 0.073(2) 0.036(3) Uani 0.25 1 d . . P B 2
C11 C 0.7070(12) 0.4277(10) 0.4771(9) 0.0296(18) Uani 1 1 d . . . . .
C12 C 0.6499(10) 0.3387(10) 0.2778(8) 0.0232(16) Uani 1 1 d . . . . .
C13 C 0.5959(10) 0.1568(10) 0.2022(9) 0.0248(17) Uani 1 1 d . . . . .
H13 H 0.594527 0.082020 0.277488 0.030 Uiso 1 1 calc R U . . .
C14 C 0.5411(11) 0.0762(9) 0.0108(10) 0.0256(17) Uani 1 1 d . . . . .
C15 C 0.5420(9) 0.1841(9) -0.0996(9) 0.0204(16) Uani 1 1 d . . . . .
C16 C 0.5960(10) 0.3773(9) -0.0192(9) 0.0215(16) Uani 1 1 d . . . . .
H16 H 0.594723 0.452371 -0.094189 0.026 Uiso 1 1 calc R U . . .
C17 C 0.6495(9) 0.4543(8) 0.1657(8) 0.0187(15) Uani 1 1 d . . . . .
C18 C 0.7069(10) 0.6470(10) 0.2500(9) 0.0238(16) Uani 1 1 d . . . . .
C19 C 0.4837(12) -0.1225(10) -0.0741(11) 0.0325(18) Uani 1 1 d . . . . .
C20 C 0.4839(10) 0.1036(9) -0.2923(10) 0.0245(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'
O O 0.0106 0.0060 '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
O1A C1 C2 129(2) . . ?
O1A C1 C6 114(2) . . ?
C2 C1 C6 116(2) . . ?
C1 C2 C3 123.1(17) . . ?
C4 C3 C2 121.9(19) . . ?
C3 C4 C5 116.6(19) . . ?
C6 C5 C10 120.9(16) . . ?
C6 C5 C4 121.6(15) . . ?
C10 C5 C4 117.4(19) . . ?
C7 C6 C5 124(2) . . ?
C7 C6 C1 116(3) . . ?
C5 C6 C1 120(2) . . ?
C6 C7 C8 116(2) . . ?
C7 C8 C9 124.4(18) . . ?
C10 C9 C8 113.0(17) . . ?
O1B C10 C9 122.6(18) . . ?
O1B C10 C5 113.6(17) . . ?
C9 C10 C5 121.1(18) . . ?
C6' C1' C2' 111.3(17) . . ?
C1' C2' C3' 122.9(17) . . ?
C4' C3' C2' 117.2(18) . . ?
C3' C4' O1C 128.3(18) . . ?
C3' C4' C5' 118.7(17) . . ?
O1C C4' C5' 107.9(17) . . ?
C6' C5' C4' 122.2(17) . . ?
C6' C5' C10' 118.9(14) . . ?
C4' C5' C10' 118.7(19) . . ?
C1' C6' C7' 115(3) . . ?
C1' C6' C5' 126.8(15) . . ?
C7' C6' C5' 118(2) . . ?
O1D C7' C6' 121(2) . . ?
O1D C7' C8' 118(2) . . ?
C6' C7' C8' 119(2) . . ?
C7' C8' C9' 120.1(19) . . ?
C10' C9' C8' 120(2) . . ?
C9' C10' C5' 122.4(19) . . ?
N1 C11 C12 178.1(8) . . ?
C13 C12 C17 120.8(6) . . ?
C13 C12 C11 121.5(7) . . ?
C17 C12 C11 117.7(7) . . ?
C12 C13 C14 119.9(7) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.4(7) . . ?
C15 C14 C19 119.0(7) . . ?
C13 C14 C19 120.6(7) . . ?
C14 C15 C20 120.6(7) . . ?
C14 C15 C16 119.7(6) . . ?
C20 C15 C16 119.7(7) . . ?
C17 C16 C15 119.6(6) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.9(7) . . ?
C16 C17 C12 119.6(6) . . ?
C18 C17 C12 119.5(6) . . ?
N2 C18 C17 178.6(8) . . ?
N4 C19 C14 179.6(9) . . ?
N3 C20 C15 178.3(8) . . ?
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 C11 1.136(10) . ?
N2 C18 1.149(9) . ?
N3 C20 1.156(9) . ?
N4 C19 1.137(10) . ?
O1A C1 1.283(14) . ?
O1B C10 1.276(13) . ?
C1 C2 1.38(3) . ?
C1 C6 1.43(3) . ?
C2 C3 1.40(3) . ?
C3 C4 1.33(2) . ?
C4 C5 1.47(3) . ?
C5 C6 1.38(4) . ?
C5 C10 1.400(14) . ?
C6 C7 1.34(3) . ?
C7 C8 1.36(2) . ?
C8 C9 1.53(3) . ?
C9 C10 1.380(14) . ?
O1C C4' 1.314(13) . ?
O1D C7' 1.267(14) . ?
C1' C6' 1.31(4) . ?
C1' C2' 1.50(2) . ?
C2' C3' 1.53(3) . ?
C3' C4' 1.31(2) . ?
C4' C5' 1.424(14) . ?
C5' C6' 1.40(3) . ?
C5' C10' 1.44(3) . ?
C6' C7' 1.393(14) . ?
C7' C8' 1.395(14) . ?
C8' C9' 1.41(3) . ?
C9' C10' 1.25(3) . ?
C11 C12 1.470(9) . ?
C12 C13 1.336(10) . ?
C12 C17 1.442(10) . ?
C13 C14 1.409(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(11) . ?
C14 C19 1.461(11) . ?
C15 C20 1.418(10) . ?
C15 C16 1.420(9) . ?
C16 C17 1.359(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.419(10) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1 C2 C3 178(2) . . . . ?
C6 C1 C2 C3 8(3) . . . . ?
C1 C2 C3 C4 -6(3) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C3 C4 C5 C6 2(4) . . . . ?
C3 C4 C5 C10 178(2) . . . . ?
C10 C5 C6 C7 2(5) . . . . ?
C4 C5 C6 C7 179(3) . . . . ?
C10 C5 C6 C1 -176(3) . . . . ?
C4 C5 C6 C1 1(4) . . . . ?
O1A C1 C6 C7 5(4) . . . . ?
C2 C1 C6 C7 176(2) . . . . ?
O1A C1 C6 C5 -177(3) . . . . ?
C2 C1 C6 C5 -6(4) . . . . ?
C5 C6 C7 C8 -1(4) . . . . ?
C1 C6 C7 C8 177(2) . . . . ?
C6 C7 C8 C9 4(3) . . . . ?
C7 C8 C9 C10 -7(3) . . . . ?
C8 C9 C10 O1B 168(2) . . . . ?
C8 C9 C10 C5 8(3) . . . . ?
C6 C5 C10 O1B -168(3) . . . . ?
C4 C5 C10 O1B 16(4) . . . . ?
C6 C5 C10 C9 -6(4) . . . . ?
C4 C5 C10 C9 177(2) . . . . ?
C6' C1' C2' C3' 3(3) . . . . ?
C1' C2' C3' C4' -9(3) . . . . ?
C2' C3' C4' O1C 162.9(19) . . . . ?
C2' C3' C4' C5' 11(3) . . . . ?
C3' C4' C5' C6' -9(4) . . . . ?
O1C C4' C5' C6' -166(3) . . . . ?
C3' C4' C5' C10' 177(2) . . . . ?
O1C C4' C5' C10' 20(3) . . . . ?
C2' C1' C6' C7' 175(2) . . . . ?
C2' C1' C6' C5' 0(4) . . . . ?
C4' C5' C6' C1' 2(5) . . . . ?
C10' C5' C6' C1' 177(3) . . . . ?
C4' C5' C6' C7' -172(3) . . . . ?
C10' C5' C6' C7' 2(4) . . . . ?
C1' C6' C7' O1D 14(4) . . . . ?
C5' C6' C7' O1D -171(3) . . . . ?
C1' C6' C7' C8' 173(2) . . . . ?
C5' C6' C7' C8' -11(4) . . . . ?
O1D C7' C8' C9' 177(2) . . . . ?
C6' C7' C8' C9' 17(4) . . . . ?
C7' C8' C9' C10' -13(3) . . . . ?
C8' C9' C10' C5' 3(3) . . . . ?
C6' C5' C10' C9' 2(4) . . . . ?
C4' C5' C10' C9' 177(2) . . . . ?
C17 C12 C13 C14 1.1(10) . . . . ?
C11 C12 C13 C14 179.7(7) . . . . ?
C12 C13 C14 C15 -0.2(11) . . . . ?
C12 C13 C14 C19 179.3(6) . . . . ?
C13 C14 C15 C20 -179.1(7) . . . . ?
C19 C14 C15 C20 1.3(10) . . . . ?
C13 C14 C15 C16 -0.8(9) . . . . ?
C19 C14 C15 C16 179.6(7) . . . . ?
C14 C15 C16 C17 1.0(8) . . . . ?
C20 C15 C16 C17 179.3(6) . . . . ?
C15 C16 C17 C18 179.1(6) . . . . ?
C15 C16 C17 C12 -0.2(8) . . . . ?
C13 C12 C17 C16 -0.8(9) . . . . ?
C11 C12 C17 C16 -179.5(6) . . . . ?
C13 C12 C17 C18 179.8(7) . . . . ?
C11 C12 C17 C18 1.1(9) . . . . ?
