#------------------------------------------------------------------------------
#$Date: 2024-07-05 20:47:42 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293226 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/32/7063211.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_7063211
loop_
_publ_author_name
'Huang, Haowen'
'Cao, Yasong'
'Zhao, Zhonghua'
'Xu, Jiatong'
'Zeng, Cheng'
'Shen, Richao'
'Lv, Jiawei'
'Lei, Ziqiang'
'Ma, Hengchang'
_publ_section_title
;
 Functionalized tails influence photoluminescence emissions for advanced
 applications in the fiel of time-resolved information input and erasure
;
_journal_issue                   23
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10748
_journal_page_last               10755
_journal_paper_doi               10.1039/D4NJ01438C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C20 H23 N O2'
_chemical_formula_sum            'C20 H23 N O2'
_chemical_formula_weight         309.39
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-13
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-11-06 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                102.303(5)
_cell_angle_beta                 109.671(5)
_cell_angle_gamma                103.453(5)
_cell_formula_units_Z            2
_cell_length_a                   8.0745(4)
_cell_length_b                   10.6294(6)
_cell_length_c                   11.2471(7)
_cell_measurement_reflns_used    4385
_cell_measurement_temperature    303.88(10)
_cell_measurement_theta_max      27.4600
_cell_measurement_theta_min      2.0810
_cell_volume                     838.09(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.88(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  64.00   1.00    0.21    --    4.16  68.00 -61.00   79
  2  ω    -17.00  37.00   1.00    0.21    --    4.16 -99.00-120.00   54
  3  ω    -16.00  30.00   1.00    0.21    --    4.16 -99.00 -90.00   46
  4  ω    -16.00  19.00   1.00    0.21    --    4.16 -99.00 120.00   35
  5  ω    -68.00  22.00   1.00    0.21    --    4.16 -68.00 164.00   90
  6  ω    -26.00   5.00   1.00    0.21    --    4.16 -37.00  30.00   31
  7  ω    -57.00  13.00   1.00    0.21    --   -6.19 -77.00  90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0103147000
_diffrn_orient_matrix_UB_12      0.0675482000
_diffrn_orient_matrix_UB_13      0.0341596000
_diffrn_orient_matrix_UB_21      -0.0370682000
_diffrn_orient_matrix_UB_22      -0.0246236000
_diffrn_orient_matrix_UB_23      0.0427430000
_diffrn_orient_matrix_UB_31      0.0910656000
_diffrn_orient_matrix_UB_32      0.0083221000
_diffrn_orient_matrix_UB_33      0.0446977000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12097
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.694
_diffrn_reflns_theta_min         2.028
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0471
_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)+(0.0522P)²+0.0555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1252
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2664
_reflns_number_total             4193
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj01438c2.cif
_cod_data_source_block           hhw_4_auto
_cod_depositor_comments
'Adding full bibliography for 7063211--7063213.cif.'
_cod_original_cell_volume        838.08(9)
_cod_database_code               7063211
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C13(H13A,
 H13B), C19(H19A,H19B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C11(H11), C8(H8), C9(H9), C5(H5), C3(H3), C10(H10), C4(H4)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.152
_oxdiff_exptl_absorpt_empirical_full_min 0.753
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15315(14) 0.14725(10) 0.09831(10) 0.0666(3) Uani 1 1 d . . . . .
O2 O -0.13237(13) 0.11533(10) -0.04445(11) 0.0693(3) Uani 1 1 d . . . . .
H2 H -0.136395 0.035452 -0.062208 0.104 Uiso 1 1 calc R U . . .
N1 N 0.98329(14) 0.94744(11) 0.64403(11) 0.0505(3) Uani 1 1 d . . . . .
C7 C 1.26311(17) 0.93020(14) 0.76198(13) 0.0480(3) Uani 1 1 d . . . . .
C1 C 1.10134(18) 1.07803(14) 0.72349(13) 0.0486(3) Uani 1 1 d . . . . .
C12 C 1.07997(17) 0.85702(14) 0.66628(13) 0.0482(3) Uani 1 1 d . . . . .
C20 C 0.03062(18) 0.19265(14) 0.05088(13) 0.0503(3) Uani 1 1 d . . . . .
C6 C 1.27719(17) 1.07160(14) 0.79712(13) 0.0487(3) Uani 1 1 d . . . . .
C14 C 0.64049(17) 0.86648(13) 0.58540(13) 0.0491(3) Uani 1 1 d . . . . .
H14A H 0.633697 0.945928 0.642332 0.059 Uiso 1 1 calc R U . . .
H14B H 0.667671 0.805697 0.636892 0.059 Uiso 1 1 calc R U . . .
C2 C 1.0694(2) 1.20165(15) 0.73309(15) 0.0610(4) Uani 1 1 d . . . . .
H2A H 0.952503 1.205448 0.685743 0.073 Uiso 1 1 calc R U . . .
C11 C 1.0216(2) 0.71677(15) 0.60862(15) 0.0602(4) Uani 1 1 d . . . . .
H11 H 0.901328 0.668734 0.544513 0.072 Uiso 1 1 calc R U . . .
C8 C 1.3869(2) 0.86012(17) 0.80124(15) 0.0605(4) Uani 1 1 d . . . . .
H8 H 1.507920 0.906909 0.864772 0.073 Uiso 1 1 calc R U . . .
C15 C 0.45260(18) 0.79362(13) 0.46603(13) 0.0518(3) Uani 1 1 d . . . . .
H15A H 0.353385 0.791271 0.496644 0.062 Uiso 1 1 calc R U . . .
H15B H 0.439591 0.845431 0.404092 0.062 Uiso 1 1 calc R U . . .
C9 C 1.3281(2) 0.72131(18) 0.74498(17) 0.0695(4) Uani 1 1 d . . . . .
H9 H 1.409760 0.673757 0.771089 0.083 Uiso 1 1 calc R U . . .
C17 C 0.24798(18) 0.57183(13) 0.27321(14) 0.0552(4) Uani 1 1 d . . . . .
H17A H 0.235409 0.620570 0.208661 0.066 Uiso 1 1 calc R U . . .
H17B H 0.145570 0.568537 0.300477 0.066 Uiso 1 1 calc R U . . .
C18 C 0.23560(19) 0.42738(14) 0.20804(14) 0.0572(4) Uani 1 1 d . . . . .
H18A H 0.331274 0.432005 0.173616 0.069 Uiso 1 1 calc R U . . .
H18B H 0.262785 0.382984 0.275818 0.069 Uiso 1 1 calc R U . . .
C13 C 0.79549(17) 0.91049(14) 0.54095(13) 0.0527(3) Uani 1 1 d . . . . .
H13A H 0.779031 0.836853 0.465649 0.063 Uiso 1 1 calc R U . . .
H13B H 0.784731 0.988250 0.510591 0.063 Uiso 1 1 calc R U . . .
C5 C 1.4232(2) 1.19222(16) 0.87832(15) 0.0643(4) Uani 1 1 d . . . . .
H5 H 1.540644 1.189867 0.926541 0.077 Uiso 1 1 calc R U . . .
C19 C 0.04929(19) 0.33959(14) 0.09579(14) 0.0564(4) Uani 1 1 d . . . . .
H19A H -0.049059 0.347761 0.124934 0.068 Uiso 1 1 calc R U . . .
H19B H 0.032248 0.373862 0.020709 0.068 Uiso 1 1 calc R U . . .
C3 C 1.2168(2) 1.31878(16) 0.81519(17) 0.0737(5) Uani 1 1 d . . . . .
H3 H 1.198706 1.402923 0.823158 0.088 Uiso 1 1 calc R U . . .
C10 C 1.1485(2) 0.65087(17) 0.64978(17) 0.0687(4) Uani 1 1 d . . . . .
H10 H 1.112438 0.556742 0.612584 0.082 Uiso 1 1 calc R U . . .
C16 C 0.43064(19) 0.64880(14) 0.39352(14) 0.0584(4) Uani 1 1 d . . . . .
H16A H 0.531840 0.651957 0.364935 0.070 Uiso 1 1 calc R U . . .
H16B H 0.443424 0.597698 0.456086 0.070 Uiso 1 1 calc R U . . .
C4 C 1.3919(2) 1.31389(18) 0.88633(18) 0.0781(5) Uani 1 1 d . . . . .
H4 H 1.489066 1.394682 0.940149 0.094 Uiso 1 1 calc R U . . .
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
C1 N1 C13 126.45(11) . . ?
C12 N1 C1 108.61(11) . . ?
C12 N1 C13 124.52(11) . . ?
C12 C7 C6 106.55(11) . . ?
C8 C7 C12 119.46(13) . . ?
C8 C7 C6 133.99(13) . . ?
N1 C1 C6 108.86(12) . . ?
N1 C1 C2 129.78(13) . . ?
C2 C1 C6 121.32(13) . . ?
N1 C12 C7 109.06(12) . . ?
N1 C12 C11 129.69(13) . . ?
C11 C12 C7 121.24(13) . . ?
O1 C20 O2 122.60(13) . . ?
O1 C20 C19 123.52(12) . . ?
O2 C20 C19 113.88(11) . . ?
C1 C6 C7 106.91(11) . . ?
C5 C6 C7 133.73(13) . . ?
C5 C6 C1 119.27(14) . . ?
C13 C14 C15 111.23(11) . . ?
C3 C2 C1 117.75(14) . . ?
C10 C11 C12 117.62(14) . . ?
C9 C8 C7 119.09(14) . . ?
C16 C15 C14 113.03(11) . . ?
C8 C9 C10 120.87(14) . . ?
C16 C17 C18 112.20(11) . . ?
C19 C18 C17 115.15(12) . . ?
N1 C13 C14 114.45(11) . . ?
C4 C5 C6 119.25(14) . . ?
C20 C19 C18 113.57(11) . . ?
C2 C3 C4 121.45(16) . . ?
C11 C10 C9 121.71(15) . . ?
C17 C16 C15 115.48(11) . . ?
C5 C4 C3 120.94(15) . . ?
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
O1 C20 1.2136(16) . ?
O2 C20 1.3146(15) . ?
N1 C1 1.3843(17) . ?
N1 C12 1.3841(16) . ?
N1 C13 1.4639(15) . ?
C7 C12 1.4095(17) . ?
C7 C6 1.437(2) . ?
C7 C8 1.3924(19) . ?
C1 C6 1.4086(18) . ?
C1 C2 1.386(2) . ?
C12 C11 1.386(2) . ?
C20 C19 1.4900(19) . ?
C6 C5 1.3930(19) . ?
C14 C15 1.5306(16) . ?
C14 C13 1.5112(19) . ?
C2 C3 1.378(2) . ?
C11 C10 1.381(2) . ?
C8 C9 1.370(2) . ?
C15 C16 1.5188(19) . ?
C9 C10 1.384(2) . ?
C17 C18 1.518(2) . ?
C17 C16 1.5161(17) . ?
C18 C19 1.5146(18) . ?
C5 C4 1.365(2) . ?
C3 C4 1.390(2) . ?
