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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/64/7226488.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_7226488
loop_
_publ_author_name
'Lifshits, Liubov M.'
'Budkina, Darya S.'
'Singh, Varun'
'Matveev, Sergey M.'
'Tarnovsky, Alexander N.'
'Klosterman, Jeremy K.'
_publ_section_title
;
 Solution-state photophysics of N-carbazolyl benzoate esters: dual
 emission and order of states in twisted push-pull chromophores.
;
_journal_issue                   39
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              27671
_journal_page_last               27683
_journal_paper_doi               10.1039/c6cp04619c
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36
_chemical_name_common            CME
_chemical_name_systematic        'CPB 2'
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-06-30 deposited with the CCDC.
2016-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.9960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.7631(5)
_cell_length_b                   3.95300(10)
_cell_length_c                   18.9724(4)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.1685
_cell_measurement_theta_min      4.3244
_cell_volume                     1533.55(6)
_computing_cell_refinement       'SAINT V8.30C (Bruker, 2013)'
_computing_data_collection       'Apex2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.30C (Bruker, 2013)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material
;
Shelxtl (Bruker, 2013),
Publcif (westrip, 2010)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker AXS D8 Quest ECO CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20952
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.282
_diffrn_reflns_theta_min         4.324
_diffrn_source                   'I-mu-S microsource X-ray tube'
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6002
_exptl_absorpt_correction_type   \^Omulti-scan\~O
_exptl_absorpt_process_details   'Apex v2014.11 (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/Hexanes'
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0423
_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)+(0.0426P)²+0.7720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2697
_reflns_number_total             3249
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cp04619c2.cif
_cod_data_source_block           CME_P21c
_cod_depositor_comments
;Adding full bibliography for 7226487--7226488.cif.

 Adding full bibliography for 7226487--7226488.cif.
;
_cod_database_code               7226488
_shelx_shelxl_version_number     2014/7
_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.
;
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
C1 C 0.19002(7) 1.0721(3) 0.53315(7) 0.0137(3) Uani 1 1 d . .
O1 O 0.48376(5) 0.4349(3) 0.63794(6) 0.0209(2) Uani 1 1 d . .
N1 N 0.22316(5) 0.9397(3) 0.48092(6) 0.0142(3) Uani 1 1 d . .
C2 C 0.21391(7) 1.1596(4) 0.60413(8) 0.0152(3) Uani 1 1 d . .
H2 H 0.2586 1.1275 0.6245 0.018 Uiso 1 1 calc R U
O2 O 0.38417(5) 0.3887(3) 0.66885(5) 0.0162(2) Uani 1 1 d . .
C3 C 0.17006(7) 1.2951(4) 0.64391(8) 0.0179(3) Uani 1 1 d . .
H3 H 0.1852 1.3588 0.6922 0.021 Uiso 1 1 calc R U
C4 C 0.10404(7) 1.3400(4) 0.61447(8) 0.0202(3) Uani 1 1 d . .
H4 H 0.0750 1.4315 0.6431 0.024 Uiso 1 1 calc R U
C5 C 0.08061(7) 1.2526(4) 0.54410(8) 0.0179(3) Uani 1 1 d . .
H5 H 0.0357 1.2829 0.5243 0.022 Uiso 1 1 calc R U
C6 C 0.12380(7) 1.1192(4) 0.50243(8) 0.0147(3) Uani 1 1 d . .
C7 C 0.11606(7) 1.0059(4) 0.42905(8) 0.0147(3) Uani 1 1 d . .
C8 C 0.06242(7) 0.9839(4) 0.37354(8) 0.0183(3) Uani 1 1 d . .
H8 H 0.0206 1.0614 0.3802 0.022 Uiso 1 1 calc R U
C9 C 0.07106(7) 0.8475(4) 0.30868(8) 0.0198(3) Uani 1 1 d . .
H9 H 0.0349 0.8324 0.2705 0.024 Uiso 1 1 calc R U
C10 C 0.13250(7) 0.7315(4) 0.29878(8) 0.0188(3) Uani 1 1 d . .
H10 H 0.1372 0.6353 0.2541 0.023 Uiso 1 1 calc R U
C11 C 0.18673(7) 0.7539(4) 0.35278(8) 0.0164(3) Uani 1 1 d . .
H11 H 0.2284 0.6754 0.3458 0.020 Uiso 1 1 calc R U
C12 C 0.17794(7) 0.8954(4) 0.41760(7) 0.0142(3) Uani 1 1 d . .
C13 C 0.29138(6) 0.8800(4) 0.48964(7) 0.0132(3) Uani 1 1 d . .
C14 C 0.32715(7) 0.9933(4) 0.43855(8) 0.0152(3) Uani 1 1 d . .
H14 H 0.3057 1.1095 0.3972 0.018 Uiso 1 1 calc R U
C15 C 0.39425(7) 0.9364(4) 0.44802(7) 0.0157(3) Uani 1 1 d . .
H15 H 0.4184 1.0099 0.4126 0.019 Uiso 1 1 calc R U
C16 C 0.42606(7) 0.7724(4) 0.50900(8) 0.0146(3) Uani 1 1 d . .
H16 H 0.4719 0.7360 0.5157 0.018 Uiso 1 1 calc R U
C17 C 0.39034(7) 0.6617(4) 0.56033(7) 0.0138(3) Uani 1 1 d . .
C18 C 0.32300(6) 0.7128(4) 0.55043(7) 0.0132(3) Uani 1 1 d . .
H18 H 0.2987 0.6336 0.5852 0.016 Uiso 1 1 calc R U
C19 C 0.42543(7) 0.4846(4) 0.62513(7) 0.0140(3) Uani 1 1 d . .
C20 C 0.41337(7) 0.2253(4) 0.73541(8) 0.0182(3) Uani 1 1 d . .
H20A H 0.4397 0.3897 0.7676 0.022 Uiso 1 1 calc R U
H20B H 0.4422 0.0376 0.7258 0.022 Uiso 1 1 calc R U
C21 C 0.35809(7) 0.0922(4) 0.76921(8) 0.0209(3) Uani 1 1 d . .
H21A H 0.3339 -0.0791 0.7379 0.031 Uiso 1 1 calc R U
H21B H 0.3287 0.2786 0.7761 0.031 Uiso 1 1 calc R U
H21C H 0.3757 -0.0095 0.8157 0.031 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 C1 N1 129.70(13)
C2 C1 C6 121.61(12)
N1 C1 C6 108.67(12)
C12 N1 C1 108.34(11)
C12 N1 C13 125.91(11)
C1 N1 C13 125.66(12)
C3 C2 C1 117.64(13)
C19 O2 C20 116.51(11)
C2 C3 C4 121.46(14)
C5 C4 C3 120.66(13)
C4 C5 C6 119.17(13)
C5 C6 C1 119.44(13)
C5 C6 C7 133.40(13)
C1 C6 C7 107.15(12)
C8 C7 C12 119.58(13)
C8 C7 C6 133.38(13)
C12 C7 C6 107.03(12)
C9 C8 C7 119.04(13)
C8 C9 C10 120.63(14)
C11 C10 C9 121.48(14)
C10 C11 C12 117.65(13)
C11 C12 N1 129.55(13)
C11 C12 C7 121.59(13)
N1 C12 C7 108.80(12)
C18 C13 C14 119.85(13)
C18 C13 N1 119.62(12)
C14 C13 N1 120.52(13)
C15 C14 C13 120.04(13)
C16 C15 C14 120.23(13)
C15 C16 C17 119.67(13)
C18 C17 C16 120.25(13)
C18 C17 C19 120.99(12)
C16 C17 C19 118.75(12)
C13 C18 C17 119.94(13)
O1 C19 O2 123.55(13)
O1 C19 C17 124.83(13)
O2 C19 C17 111.62(11)
O2 C20 C21 106.96(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.395(2)
C1 N1 1.4020(17)
C1 C6 1.4095(19)
O1 C19 1.2092(17)
N1 C12 1.4014(18)
N1 C13 1.4173(17)
C2 C3 1.387(2)
O2 C19 1.3463(16)
O2 C20 1.4539(17)
C3 C4 1.399(2)
C4 C5 1.383(2)
C5 C6 1.398(2)
C6 C7 1.445(2)
C7 C8 1.396(2)
C7 C12 1.4090(19)
C8 C9 1.383(2)
C9 C10 1.398(2)
C10 C11 1.387(2)
C11 C12 1.392(2)
C13 C18 1.3910(19)
C13 C14 1.3934(19)
C14 C15 1.392(2)
C15 C16 1.389(2)
C16 C17 1.3930(19)
C17 C18 1.3928(19)
C17 C19 1.490(2)
C20 C21 1.504(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101886207
