#------------------------------------------------------------------------------
#$Date: 2024-07-05 20:52:47 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293232 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159958.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_7159958
loop_
_publ_author_name
'Arora, Aditi'
'Kumar, Sumit'
'Kumar, Sandeep'
'Dua, Amita'
'Singh, Brajendra K.'
_publ_section_title
;
 Synthesis, characterization and photophysical studies of dual-emissive
 base-modified fluorescent nucleosides.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4922
_journal_page_last               4939
_journal_paper_doi               10.1039/d4ob00749b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H14 N4 O3'
_chemical_formula_sum            'C18 H14 N4 O3'
_chemical_formula_weight         334.33
_chemical_name_systematic
4-(azidomethyl)-N9-phenyl-9,10-dihydro-2H,8H-chromeno[8,7-e][1,3]oxazin-2-one
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-03-27 deposited with the CCDC.	2024-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.777(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1867(6)
_cell_length_b                   14.9870(6)
_cell_length_c                   8.0323(4)
_cell_measurement_reflns_used    8289
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.3060
_cell_measurement_theta_min      3.2960
_cell_volume                     1568.83(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  27.00   0.50   10.47    --   -5.68 -99.00   0.00  100
  2  ω    -23.00  27.00   0.50   10.47    --   -5.68 -99.00 -30.00  100
  3  ω    -28.00  67.00   0.50   10.47    --   -5.68  77.00 -30.00  190
  4  ω    -23.00  38.00   0.50   10.47    --    5.83 -99.00-180.00  122
  5  ω    -81.00  -5.00   0.50   10.47    --   -5.68 -19.00-120.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0421740000
_diffrn_orient_matrix_UB_12      0.0228589000
_diffrn_orient_matrix_UB_13      -0.0466832000
_diffrn_orient_matrix_UB_21      -0.0297594000
_diffrn_orient_matrix_UB_22      -0.0395313000
_diffrn_orient_matrix_UB_23      -0.0030844000
_diffrn_orient_matrix_UB_31      -0.0172858000
_diffrn_orient_matrix_UB_32      0.0124049000
_diffrn_orient_matrix_UB_33      0.0761358000
_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  0.0372
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18230
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.046
_diffrn_reflns_theta_min         3.136
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_preparation
'Slow evaporation in methaol and chloroform mixture'
_exptl_crystal_recrystallization_method Evaporation
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0457
_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)+(0.0573P)²+0.1447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2829
_reflns_number_total             4134
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00749b2.cif
_cod_data_source_block           akp-a-6171_auto
_cod_depositor_comments          'Adding full bibliography for 7159958.cif.'
_cod_database_code               7159958
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C N O H'
_chemical_oxdiff_usercomment     02.12.2022
_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_max   0.990
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C16(H16), C6(H6), C12(H12), C15(H15), C14(H14), C13(H13)
;
_olex2_submission_original_sample_id AKP-A-6171
_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 1.652
_oxdiff_exptl_absorpt_empirical_full_min 0.597
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61286(7) 0.63871(6) 0.10589(11) 0.0389(2) Uani 1 1 d . . . . .
O2 O 0.55975(8) 0.75268(6) -0.05758(14) 0.0517(3) Uani 1 1 d . . . . .
O3 O 0.74320(8) 0.39976(6) 0.46516(13) 0.0483(3) Uani 1 1 d . . . . .
N1 N 0.85452(8) 0.52367(7) 0.43490(14) 0.0404(3) Uani 1 1 d . . . . .
C4 C 0.49333(10) 0.53567(8) 0.20292(15) 0.0361(3) Uani 1 1 d . . . . .
C9 C 0.59334(10) 0.56449(8) 0.19725(15) 0.0347(3) Uani 1 1 d . . . . .
N2 N 0.22371(10) 0.61503(11) 0.02841(19) 0.0639(4) Uani 1 1 d . . . . .
C17 C 0.85128(9) 0.56869(8) 0.59098(16) 0.0367(3) Uani 1 1 d . . . . .
C7 C 0.66378(11) 0.44544(8) 0.37307(16) 0.0391(3) Uani 1 1 d . . . . .
C2 C 0.43077(10) 0.66168(9) 0.03067(17) 0.0415(3) Uani 1 1 d . . . . .
H2 H 0.376539 0.695765 -0.023151 0.050 Uiso 1 1 calc R U . . .
C1 C 0.53460(10) 0.68919(8) 0.01979(17) 0.0396(3) Uani 1 1 d . . . . .
C3 C 0.41002(10) 0.58838(9) 0.11611(16) 0.0387(3) Uani 1 1 d . . . . .
C8 C 0.67965(10) 0.52187(8) 0.28230(16) 0.0368(3) Uani 1 1 d . . . . .
C5 C 0.48189(11) 0.45798(9) 0.29609(17) 0.0416(3) Uani 1 1 d . . . . .
H5 H 0.416356 0.436248 0.301005 0.050 Uiso 1 1 calc R U . . .
N3 N 0.17872(12) 0.66565(11) 0.1103(2) 0.0709(4) Uani 1 1 d . . . . .
C16 C 0.77788(10) 0.63299(9) 0.61139(18) 0.0414(3) Uani 1 1 d . . . . .
H16 H 0.726305 0.646479 0.522518 0.050 Uiso 1 1 calc R U . . .
C6 C 0.56490(11) 0.41366(9) 0.37964(17) 0.0431(3) Uani 1 1 d . . . . .
H6 H 0.555597 0.362402 0.440800 0.052 Uiso 1 1 calc R U . . .
C10 C 0.78717(10) 0.55776(9) 0.28687(17) 0.0412(3) Uani 1 1 d . . . . .
H10A H 0.813465 0.539925 0.185493 0.049 Uiso 1 1 calc R U . . .
H10B H 0.785878 0.622441 0.290550 0.049 Uiso 1 1 calc R U . . .
C12 C 0.92673(11) 0.54918(10) 0.72735(18) 0.0460(3) Uani 1 1 d . . . . .
H12 H 0.975477 0.505556 0.716667 0.055 Uiso 1 1 calc R U . . .
C15 C 0.78172(12) 0.67683(9) 0.7640(2) 0.0494(4) Uani 1 1 d . . . . .
H15 H 0.732300 0.719544 0.776674 0.059 Uiso 1 1 calc R U . . .
C11 C 0.84536(11) 0.42860(10) 0.43935(19) 0.0470(3) Uani 1 1 d . . . . .
H11A H 0.895639 0.405244 0.529598 0.056 Uiso 1 1 calc R U . . .
H11B H 0.860426 0.404007 0.334129 0.056 Uiso 1 1 calc R U . . .
C18 C 0.30206(11) 0.55925(11) 0.12838(19) 0.0488(4) Uani 1 1 d . . . . .
H18A H 0.293090 0.497935 0.090299 0.059 Uiso 1 1 calc R U . . .
H18B H 0.292041 0.561125 0.245477 0.059 Uiso 1 1 calc R U . . .
C14 C 0.85736(14) 0.65826(11) 0.8972(2) 0.0562(4) Uani 1 1 d . . . . .
H14 H 0.859748 0.688551 0.998798 0.067 Uiso 1 1 calc R U . . .
C13 C 0.92973(13) 0.59399(11) 0.8780(2) 0.0552(4) Uani 1 1 d . . . . .
H13 H 0.981008 0.580796 0.967478 0.066 Uiso 1 1 calc R U . . .
N4 N 0.1299(2) 0.71308(15) 0.1726(4) 0.1236(8) 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
C1 O1 C9 121.60(10) . . ?
C7 O3 C11 114.93(10) . . ?
C17 N1 C10 116.87(11) . . ?
C17 N1 C11 115.72(11) . . ?
C11 N1 C10 108.96(11) . . ?
C9 C4 C3 117.93(11) . . ?
C9 C4 C5 116.94(12) . . ?
C5 C4 C3 125.13(12) . . ?
O1 C9 C4 121.44(12) . . ?
O1 C9 C8 115.28(11) . . ?
C8 C9 C4 123.28(11) . . ?
N3 N2 C18 114.81(15) . . ?
C16 C17 N1 122.94(12) . . ?
C16 C17 C12 118.56(13) . . ?
C12 C17 N1 118.47(11) . . ?
O3 C7 C8 122.07(12) . . ?
O3 C7 C6 116.77(11) . . ?
C8 C7 C6 121.11(13) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C3 C2 C1 122.14(13) . . ?
O1 C1 C2 117.20(11) . . ?
O2 C1 O1 116.53(12) . . ?
O2 C1 C2 126.27(13) . . ?
C4 C3 C18 117.84(12) . . ?
C2 C3 C4 119.62(12) . . ?
C2 C3 C18 122.53(13) . . ?
C9 C8 C7 117.30(12) . . ?
C9 C8 C10 122.88(11) . . ?
C7 C8 C10 119.74(12) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.45(12) . . ?
C6 C5 H5 119.3 . . ?
N4 N3 N2 173.2(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.01(14) . . ?
C15 C16 H16 120.0 . . ?
C7 C6 H6 120.1 . . ?
C5 C6 C7 119.89(12) . . ?
C5 C6 H6 120.1 . . ?
N1 C10 C8 110.25(10) . . ?
N1 C10 H10A 109.6 . . ?
N1 C10 H10B 109.6 . . ?
C8 C10 H10A 109.6 . . ?
C8 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C17 C12 H12 119.7 . . ?
C13 C12 C17 120.59(13) . . ?
C13 C12 H12 119.7 . . ?
C16 C15 H15 119.4 . . ?
C14 C15 C16 121.11(14) . . ?
C14 C15 H15 119.4 . . ?
O3 C11 H11A 109.1 . . ?
O3 C11 H11B 109.1 . . ?
N1 C11 O3 112.44(11) . . ?
N1 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N2 C18 C3 113.09(13) . . ?
N2 C18 H18A 109.0 . . ?
N2 C18 H18B 109.0 . . ?
C3 C18 H18A 109.0 . . ?
C3 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C15 C14 H14 120.5 . . ?
C15 C14 C13 119.05(14) . . ?
C13 C14 H14 120.5 . . ?
C12 C13 C14 120.67(15) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
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 C9 1.3783(14) . ?
O1 C1 1.3776(16) . ?
O2 C1 1.2102(15) . ?
O3 C7 1.3697(17) . ?
O3 C11 1.4595(17) . ?
N1 C17 1.4300(17) . ?
N1 C10 1.4634(17) . ?
N1 C11 1.4307(18) . ?
C4 C9 1.3951(18) . ?
C4 C3 1.4434(19) . ?
C4 C5 1.4045(18) . ?
C9 C8 1.3903(19) . ?
N2 N3 1.216(2) . ?
N2 C18 1.469(2) . ?
C17 C16 1.3931(18) . ?
C17 C12 1.394(2) . ?
C7 C8 1.3906(18) . ?
C7 C6 1.3967(19) . ?
C2 H2 0.9300 . ?
C2 C1 1.4452(19) . ?
C2 C3 1.3454(19) . ?
C3 C18 1.5066(19) . ?
C8 C10 1.5118(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.366(2) . ?
N3 N4 1.126(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.385(2) . ?
C6 H6 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C13 1.379(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.375(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C13 1.381(2) . ?
C13 H13 0.9300 . ?
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 C9 C8 C7 -178.57(10) . . . . ?
O1 C9 C8 C10 4.74(18) . . . . ?
O3 C7 C8 C9 -178.14(11) . . . . ?
O3 C7 C8 C10 -1.34(19) . . . . ?
O3 C7 C6 C5 177.49(11) . . . . ?
N1 C17 C16 C15 -177.23(12) . . . . ?
N1 C17 C12 C13 176.84(13) . . . . ?
C4 C9 C8 C7 1.77(19) . . . . ?
C4 C9 C8 C10 -174.92(11) . . . . ?
C4 C3 C18 N2 -177.09(12) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C9 O1 C1 O2 -179.51(11) . . . . ?
C9 O1 C1 C2 0.68(17) . . . . ?
C9 C4 C3 C2 1.31(18) . . . . ?
C9 C4 C3 C18 -177.52(11) . . . . ?
C9 C4 C5 C6 1.11(19) . . . . ?
C9 C8 C10 N1 156.33(12) . . . . ?
C17 N1 C10 C8 -81.71(14) . . . . ?
C17 N1 C11 O3 68.72(15) . . . . ?
C17 C16 C15 C14 0.2(2) . . . . ?
C17 C12 C13 C14 0.8(2) . . . . ?
C7 O3 C11 N1 43.14(16) . . . . ?
C7 C8 C10 N1 -20.28(17) . . . . ?
C2 C3 C18 N2 4.1(2) . . . . ?
C1 O1 C9 C4 1.78(17) . . . . ?
C1 O1 C9 C8 -177.88(11) . . . . ?
C1 C2 C3 C4 1.14(19) . . . . ?
C1 C2 C3 C18 179.91(12) . . . . ?
C3 C4 C9 O1 -2.77(17) . . . . ?
C3 C4 C9 C8 176.86(11) . . . . ?
C3 C4 C5 C6 -177.63(12) . . . . ?
C3 C2 C1 O1 -2.15(19) . . . . ?
C3 C2 C1 O2 178.06(13) . . . . ?
C8 C7 C6 C5 -0.1(2) . . . . ?
C5 C4 C9 O1 178.39(11) . . . . ?
C5 C4 C9 C8 -1.97(19) . . . . ?
C5 C4 C3 C2 -179.96(12) . . . . ?
C5 C4 C3 C18 1.21(19) . . . . ?
N3 N2 C18 C3 -106.26(16) . . . . ?
C16 C17 C12 C13 -1.3(2) . . . . ?
C16 C15 C14 C13 -0.7(2) . . . . ?
C6 C7 C8 C9 -0.70(19) . . . . ?
C6 C7 C8 C10 176.11(12) . . . . ?
C10 N1 C17 C16 9.62(17) . . . . ?
C10 N1 C17 C12 -168.47(12) . . . . ?
C10 N1 C11 O3 -65.38(14) . . . . ?
C12 C17 C16 C15 0.86(19) . . . . ?
C15 C14 C13 C12 0.3(2) . . . . ?
C11 O3 C7 C8 -9.33(18) . . . . ?
C11 O3 C7 C6 173.13(11) . . . . ?
C11 N1 C17 C16 -120.79(14) . . . . ?
C11 N1 C17 C12 61.12(16) . . . . ?
C11 N1 C10 C8 51.80(14) . . . . ?
