#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:38:24 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286102 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/70/7247049.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_7247049
loop_
_publ_author_name
'Gogoi, Gayatri'
'Sarma, Rupam J.'
_publ_section_title
;
 Effect of twisted molecular geometry on the solid-state emissions of an
 anthracene fluorophore
;
_journal_issue                   32
_journal_name_full               CrystEngComm
_journal_page_first              4582
_journal_page_last               4591
_journal_paper_doi               10.1039/D3CE00481C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C22 H18 N2 O3'
_chemical_formula_sum            'C22 H18 N2 O3'
_chemical_formula_weight         358.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2023-05-09 deposited with the CCDC.	2023-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5066(4)
_cell_length_b                   14.8096(5)
_cell_length_c                   18.3306(7)
_cell_measurement_reflns_used    6087
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.40
_cell_volume                     3395.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_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  0.0281
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18823
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.082
_diffrn_reflns_theta_min         2.404
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.988
_exptl_transmission_factor_min   0.981
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0466
_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)+(0.0591P)²+0.8074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3354
_reflns_number_total             4469
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00481c2.cif
_cod_data_source_block           rjs_9an_4oh_0m
_cod_depositor_comments
'Adding full bibliography for 7247048--7247050.cif.'
_cod_database_code               7247049
_shelx_shelxl_version_number     2016/6
_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   0.980
_shelx_estimated_absorpt_t_max   0.989
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
C1 C 1.06739(10) 0.22814(9) 0.21959(7) 0.0321(3) Uani 1 1 d . . . . .
C2 C 1.11776(11) 0.28668(11) 0.26749(8) 0.0403(4) Uani 1 1 d . . . . .
H2 H 1.188587 0.303201 0.259688 0.048 Uiso 1 1 calc R U . . .
C3 C 1.06309(11) 0.32028(10) 0.32646(8) 0.0371(3) Uani 1 1 d . . . . .
H3 H 1.097595 0.359644 0.358218 0.045 Uiso 1 1 calc R U . . .
C4 C 0.95722(10) 0.29676(9) 0.33975(7) 0.0277(3) Uani 1 1 d . . . . .
C5 C 0.90741(10) 0.23827(9) 0.29114(8) 0.0322(3) Uani 1 1 d . . . . .
H5 H 0.836730 0.221381 0.299037 0.039 Uiso 1 1 calc R U . . .
C6 C 0.96137(11) 0.20505(10) 0.23144(8) 0.0353(3) Uani 1 1 d . . . . .
H6 H 0.926533 0.166904 0.198893 0.042 Uiso 1 1 calc R U . . .
C7 C 0.90478(10) 0.33931(9) 0.40366(7) 0.0301(3) Uani 1 1 d . . . . .
C8 C 0.65349(11) 0.33585(10) 0.48384(8) 0.0353(3) Uani 1 1 d . . . . .
H8 H 0.628215 0.286929 0.457115 0.042 Uiso 1 1 calc R U . . .
C9 C 0.58029(10) 0.37939(9) 0.53551(7) 0.0294(3) Uani 1 1 d . . . . .
C10 C 0.46956(10) 0.37747(9) 0.51735(7) 0.0294(3) Uani 1 1 d . . . . .
C11 C 0.42779(12) 0.33531(10) 0.45352(8) 0.0382(3) Uani 1 1 d . . . . .
H11 H 0.474467 0.306582 0.421569 0.046 Uiso 1 1 calc R U . . .
C12 C 0.32151(12) 0.33604(11) 0.43820(9) 0.0444(4) Uani 1 1 d . . . . .
H12 H 0.296678 0.307532 0.396288 0.053 Uiso 1 1 calc R U . . .
C13 C 0.24826(12) 0.37959(12) 0.48516(9) 0.0450(4) Uani 1 1 d . . . . .
H13 H 0.175652 0.379553 0.474213 0.054 Uiso 1 1 calc R U . . .
C14 C 0.28374(11) 0.42104(10) 0.54565(9) 0.0385(3) Uani 1 1 d . . . . .
H14 H 0.235015 0.449743 0.576158 0.046 Uiso 1 1 calc R U . . .
C15 C 0.39448(10) 0.42202(9) 0.56414(8) 0.0314(3) Uani 1 1 d . . . . .
C16 C 0.43067(11) 0.46607(10) 0.62601(8) 0.0358(3) Uani 1 1 d . . . . .
H16 H 0.381542 0.496047 0.655400 0.043 Uiso 1 1 calc R U . . .
C17 C 0.53790(11) 0.46695(9) 0.64564(8) 0.0328(3) Uani 1 1 d . . . . .
C18 C 0.57189(13) 0.51052(11) 0.71067(9) 0.0441(4) Uani 1 1 d . . . . .
H18 H 0.521647 0.539400 0.739904 0.053 Uiso 1 1 calc R U . . .
C19 C 0.67552(14) 0.51083(12) 0.73084(9) 0.0481(4) Uani 1 1 d . . . . .
C20 C 0.75227(14) 0.46739(12) 0.68668(9) 0.0457(4) Uani 1 1 d . . . . .
C21 C 0.72367(12) 0.42499(11) 0.62392(9) 0.0386(3) Uani 1 1 d . . . . .
C22 C 0.61503(10) 0.42281(9) 0.60000(7) 0.0299(3) Uani 1 1 d . . . . .
H19 H 0.6974(13) 0.5384(12) 0.7761(11) 0.053(5) Uiso 1 1 d . . . . .
H20 H 0.8266(16) 0.4699(12) 0.7003(10) 0.053(5) Uiso 1 1 d . . . . .
H21 H 0.7775(14) 0.3981(11) 0.5967(10) 0.044(5) Uiso 1 1 d . . . . .
N1 N 0.80296(9) 0.31586(8) 0.41849(7) 0.0336(3) Uani 1 1 d . . . . .
N2 N 0.74921(9) 0.36099(8) 0.47346(7) 0.0354(3) Uani 1 1 d . . . . .
O1 O 1.12443(9) 0.19632(8) 0.16196(6) 0.0422(3) Uani 1 1 d . . . . .
O2 O 0.95234(9) 0.39571(8) 0.44070(6) 0.0472(3) Uani 1 1 d . . . . .
O3 O 1.00235(10) 0.42055(10) 0.58760(7) 0.0510(3) Uani 1 1 d . . . . .
H1N H 0.7680(13) 0.2714(11) 0.3935(9) 0.043(4) Uiso 1 1 d . . . . .
H1O H 1.0857(15) 0.1566(14) 0.1373(11) 0.060(6) Uiso 1 1 d . . . . .
H3B H 1.0162(18) 0.4773(18) 0.5838(13) 0.076(7) Uiso 1 1 d . . . . .
H3A H 0.9755(18) 0.4084(15) 0.5428(15) 0.076(7) Uiso 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
O1 C1 C2 118.09(12) . . ?
O1 C1 C6 122.57(13) . . ?
C2 C1 C6 119.33(12) . . ?
C3 C2 C1 119.97(12) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 121.43(13) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.06(12) . . ?
C5 C4 C7 124.96(11) . . ?
C3 C4 C7 116.93(12) . . ?
C6 C5 C4 120.84(12) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.35(13) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O2 C7 N1 121.38(13) . . ?
O2 C7 C4 120.72(12) . . ?
N1 C7 C4 117.87(12) . . ?
N2 C8 C9 123.86(13) . . ?
N2 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?
C22 C9 C10 120.20(12) . . ?
C22 C9 C8 123.23(12) . . ?
C10 C9 C8 116.56(12) . . ?
C9 C10 C11 123.83(12) . . ?
C9 C10 C15 119.22(12) . . ?
C11 C10 C15 116.93(12) . . ?
C12 C11 C10 121.65(14) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.79(15) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.83(14) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 121.46(14) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 121.14(13) . . ?
C16 C15 C10 119.54(12) . . ?
C14 C15 C10 119.32(13) . . ?
C15 C16 C17 122.17(12) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C16 C17 C18 120.71(13) . . ?
C16 C17 C22 119.61(13) . . ?
C18 C17 C22 119.68(13) . . ?
C19 C18 C17 121.30(14) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 119.69(15) . . ?
C18 C19 H19 120.7(10) . . ?
C20 C19 H19 119.6(10) . . ?
C21 C20 C19 121.16(15) . . ?
C21 C20 H20 119.4(11) . . ?
C19 C20 H20 119.4(11) . . ?
C20 C21 C22 121.39(14) . . ?
C20 C21 H21 117.5(11) . . ?
C22 C21 H21 121.1(11) . . ?
C9 C22 C21 124.01(12) . . ?
C9 C22 C17 119.22(12) . . ?
C21 C22 C17 116.77(13) . . ?
C7 N1 N2 118.78(12) . . ?
C7 N1 H1N 122.5(10) . . ?
N2 N1 H1N 118.7(10) . . ?
C8 N2 N1 115.23(12) . . ?
C1 O1 H1O 109.9(13) . . ?
H3B O3 H3A 101(2) . . ?
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
C1 O1 1.3591(16) . ?
C1 C2 1.386(2) . ?
C1 C6 1.3864(19) . ?
C2 C3 1.372(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.3907(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.3901(19) . ?
C4 C7 1.4831(18) . ?
C5 C6 1.3766(19) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.2298(16) . ?
C7 N1 1.3477(17) . ?
C8 N2 1.2681(18) . ?
C8 C9 1.4666(18) . ?
C8 H8 0.9300 . ?
C9 C22 1.4140(19) . ?
C9 C10 1.4247(18) . ?
C10 C11 1.425(2) . ?
C10 C15 1.4326(18) . ?
C11 C12 1.359(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.413(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.343(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.4258(19) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(2) . ?
C16 C17 1.389(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.421(2) . ?
C17 C22 1.4345(18) . ?
C18 C19 1.348(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.411(2) . ?
C19 H19 0.964(19) . ?
C20 C21 1.359(2) . ?
C20 H20 0.963(19) . ?
C21 C22 1.4281(19) . ?
C21 H21 0.927(18) . ?
N1 N2 1.3834(15) . ?
N1 H1N 0.914(17) . ?
O1 H1O 0.89(2) . ?
O3 H3B 0.86(3) . ?
O3 H3A 0.90(3) . ?
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
O1 C1 C2 C3 -179.90(14) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C2 C3 C4 C7 -178.07(14) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C7 C4 C5 C6 177.17(13) . . . . ?
C4 C5 C6 C1 1.2(2) . . . . ?
O1 C1 C6 C5 179.25(13) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
C5 C4 C7 O2 -174.34(13) . . . . ?
C3 C4 C7 O2 3.1(2) . . . . ?
C5 C4 C7 N1 4.0(2) . . . . ?
C3 C4 C7 N1 -178.52(13) . . . . ?
N2 C8 C9 C22 -29.7(2) . . . . ?
N2 C8 C9 C10 149.41(14) . . . . ?
C22 C9 C10 C11 179.96(13) . . . . ?
C8 C9 C10 C11 0.83(19) . . . . ?
C22 C9 C10 C15 1.63(19) . . . . ?
C8 C9 C10 C15 -177.50(12) . . . . ?
C9 C10 C11 C12 -179.34(14) . . . . ?
C15 C10 C11 C12 -1.0(2) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C16 179.01(14) . . . . ?
C13 C14 C15 C10 -0.3(2) . . . . ?
C9 C10 C15 C16 0.01(19) . . . . ?
C11 C10 C15 C16 -178.43(13) . . . . ?
C9 C10 C15 C14 179.31(12) . . . . ?
C11 C10 C15 C14 0.87(19) . . . . ?
C14 C15 C16 C17 179.15(13) . . . . ?
C10 C15 C16 C17 -1.6(2) . . . . ?
C15 C16 C17 C18 -178.10(14) . . . . ?
C15 C16 C17 C22 1.4(2) . . . . ?
C16 C17 C18 C19 179.10(16) . . . . ?
C22 C17 C18 C19 -0.4(2) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C10 C9 C22 C21 177.44(13) . . . . ?
C8 C9 C22 C21 -3.5(2) . . . . ?
C10 C9 C22 C17 -1.76(19) . . . . ?
C8 C9 C22 C17 177.31(13) . . . . ?
C20 C21 C22 C9 -179.62(15) . . . . ?
C20 C21 C22 C17 -0.4(2) . . . . ?
C16 C17 C22 C9 0.25(19) . . . . ?
C18 C17 C22 C9 179.79(13) . . . . ?
C16 C17 C22 C21 -179.01(14) . . . . ?
C18 C17 C22 C21 0.5(2) . . . . ?
O2 C7 N1 N2 4.5(2) . . . . ?
C4 C7 N1 N2 -173.88(12) . . . . ?
C9 C8 N2 N1 -175.24(13) . . . . ?
C7 N1 N2 C8 179.38(13) . . . . ?
