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#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/58/7155829.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_7155829
loop_
_publ_author_name
'Sarkar, Sujan K.'
'Gatlin, DeVonna M'
'Das, Anushree'
'Loftin, Breyinn'
'Krause, Jeanette'
'Abe, Manabu'
'Gudmundsdottir , Anna'
_publ_section_title
;
 Laser flash photolysis of nanocrystalline α-azido-p-methoxy-acetophenone
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01731F
_journal_year                    2017
_chemical_formula_moiety         'C17 H17 N O4'
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.31
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-07-11 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.010(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.431(3)
_cell_length_b                   5.3912(9)
_cell_length_c                   16.311(3)
_cell_measurement_reflns_used    3178
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.13
_cell_measurement_theta_min      2.71
_cell_volume                     1441.3(4)
_computing_cell_refinement       'Bruker SAINT v8.32B'
_computing_data_collection       'Bruker APEX2 v2013.6.2'
_computing_data_reduction        'Bruker SAINT v8.32B'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'
_computing_structure_refinement
'Bruker SHELXTL v6.14 & SHELXL-2014/7 (Sheldrick, 2014)''
_computing_structure_solution    'Bruker SHELXTL v6.14'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker AXS APEXII CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7749
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17437
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        27.706
_diffrn_reflns_theta_max         31.131
_diffrn_reflns_theta_min         1.355
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9988
_exptl_absorpt_correction_T_min  0.9953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2012/1 (Sheldrick)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       rod
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0424
_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)+(0.0557P)²+0.3057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2536
_reflns_number_total             3525
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ob01731f2.cif
_cod_data_source_block           7
_cod_database_code               7155829
_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.
;
_shelx_estimated_absorpt_t_min   0.995
_shelx_estimated_absorpt_t_max   0.999
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
O1 O 0.19554(6) 0.44301(19) 0.47419(6) 0.0290(3) Uani 1 1 d . .
O2 O 0.51607(6) 0.7625(2) 0.68144(7) 0.0350(3) Uani 1 1 d . .
O3 O 0.69870(6) 0.0806(2) 0.67762(7) 0.0362(3) Uani 1 1 d . .
O4 O 0.99732(6) 0.56572(19) 0.87889(6) 0.0295(3) Uani 1 1 d . .
N1 N 0.64245(7) 0.4582(2) 0.68567(8) 0.0285(3) Uani 1 1 d . .
H1 H 0.6427(10) 0.619(3) 0.6967(10) 0.034 Uiso 1 1 d . U
C1 C 0.17689(9) 0.2314(3) 0.42378(9) 0.0310(3) Uani 1 1 d . .
H1A H 0.1217 0.2484 0.3974 0.047 Uiso 1 1 calc R U
H1B H 0.1798 0.0814 0.4578 0.047 Uiso 1 1 calc R U
H1C H 0.2163 0.2191 0.3815 0.047 Uiso 1 1 calc R U
C2 C 0.27149(8) 0.4545(3) 0.51354(8) 0.0230(3) Uani 1 1 d . .
C3 C 0.33270(8) 0.2796(3) 0.50521(9) 0.0252(3) Uani 1 1 d . .
H3 H 0.3235 0.1399 0.4703 0.030 Uiso 1 1 calc R U
C4 C 0.40762(8) 0.3137(3) 0.54910(9) 0.0260(3) Uani 1 1 d . .
H4 H 0.4494 0.1938 0.5445 0.031 Uiso 1 1 calc R U
C5 C 0.42274(8) 0.5193(3) 0.59946(8) 0.0224(3) Uani 1 1 d . .
C6 C 0.35990(8) 0.6909(3) 0.60679(9) 0.0262(3) Uani 1 1 d . .
H6 H 0.3689 0.8318 0.6412 0.031 Uiso 1 1 calc R U
C7 C 0.28515(8) 0.6581(3) 0.56474(9) 0.0278(3) Uani 1 1 d . .
H7 H 0.2428 0.7751 0.5708 0.033 Uiso 1 1 calc R U
C8 C 0.50246(8) 0.5690(3) 0.64450(8) 0.0244(3) Uani 1 1 d . .
C9 C 0.56757(8) 0.3725(3) 0.64287(9) 0.0263(3) Uani 1 1 d . .
H9A H 0.5488 0.2195 0.6694 0.032 Uiso 1 1 calc R U
H9B H 0.5776 0.3325 0.5852 0.032 Uiso 1 1 calc R U
C10 C 0.70430(8) 0.2984(3) 0.70048(9) 0.0260(3) Uani 1 1 d . .
C11 C 0.77993(8) 0.3917(3) 0.74673(8) 0.0234(3) Uani 1 1 d . .
C12 C 0.85082(8) 0.2516(3) 0.74128(9) 0.0272(3) Uani 1 1 d . .
H12 H 0.8498 0.1092 0.7069 0.033 Uiso 1 1 calc R U
C13 C 0.92200(8) 0.3173(3) 0.78504(9) 0.0274(3) Uani 1 1 d . .
H13 H 0.9701 0.2224 0.7799 0.033 Uiso 1 1 calc R U
C14 C 0.92393(8) 0.5219(3) 0.83672(8) 0.0232(3) Uani 1 1 d . .
C15 C 0.85431(8) 0.6672(3) 0.84243(9) 0.0244(3) Uani 1 1 d . .
H15 H 0.8555 0.8090 0.8771 0.029 Uiso 1 1 calc R U
C16 C 0.78298(8) 0.6010(3) 0.79657(8) 0.0242(3) Uani 1 1 d . .
H16 H 0.7356 0.7006 0.7994 0.029 Uiso 1 1 calc R U
C17 C 1.00385(9) 0.7771(3) 0.93152(10) 0.0335(4) Uani 1 1 d . .
H17A H 1.0599 0.7905 0.9560 0.050 Uiso 1 1 calc R U
H17B H 0.9662 0.7591 0.9752 0.050 Uiso 1 1 calc R U
H17C H 0.9900 0.9270 0.8995 0.050 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 0.0040 0.0020 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0076 0.0040 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
O O 0.0132 0.0074 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 C1 117.39(11)
C14 O4 C17 117.89(11)
C10 N1 C9 119.31(13)
O1 C2 C7 115.04(12)
O1 C2 C3 124.51(13)
C7 C2 C3 120.45(12)
C2 C3 C4 118.63(13)
C5 C4 C3 121.59(13)
C4 C5 C6 118.37(12)
C4 C5 C8 123.52(12)
C6 C5 C8 118.09(12)
C7 C6 C5 120.74(13)
C6 C7 C2 120.20(13)
O2 C8 C5 121.74(13)
O2 C8 C9 120.33(12)
C5 C8 C9 117.94(12)
N1 C9 C8 110.34(12)
O3 C10 N1 121.15(13)
O3 C10 C11 120.99(13)
N1 C10 C11 117.85(13)
C16 C11 C12 118.71(12)
C16 C11 C10 124.28(13)
C12 C11 C10 116.96(13)
C13 C12 C11 120.74(13)
C12 C13 C14 120.23(13)
O4 C14 C13 115.17(12)
O4 C14 C15 124.63(13)
C13 C14 C15 120.20(12)
C16 C15 C14 118.93(13)
C11 C16 C15 121.14(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3642(15)
O1 C1 1.4269(17)
O2 C8 1.2178(17)
O3 C10 1.2333(18)
O4 C14 1.3664(15)
O4 C17 1.4264(18)
N1 C10 1.3414(18)
N1 C9 1.4473(17)
C2 C7 1.388(2)
C2 C3 1.3922(19)
C3 C4 1.3922(18)
C4 C5 1.3913(19)
C5 C6 1.3978(19)
C5 C8 1.4808(18)
C6 C7 1.3756(19)
C8 C9 1.507(2)
C10 C11 1.4951(18)
C11 C16 1.389(2)
C11 C12 1.3962(19)
C12 C13 1.3734(19)
C13 C14 1.387(2)
C14 C15 1.3948(19)
C15 C16 1.3920(18)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.886(18) 2.679(18) 3.4854(18) 151.9(14) 1_565
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
C1 O1 C2 C7 -177.11(13)
C1 O1 C2 C3 2.7(2)
O1 C2 C3 C4 -179.93(13)
C7 C2 C3 C4 -0.1(2)
C2 C3 C4 C5 -1.1(2)
C3 C4 C5 C6 1.4(2)
C3 C4 C5 C8 -177.31(14)
C4 C5 C6 C7 -0.5(2)
C8 C5 C6 C7 178.31(14)
C5 C6 C7 C2 -0.7(2)
O1 C2 C7 C6 -179.15(13)
C3 C2 C7 C6 1.0(2)
C4 C5 C8 O2 172.57(14)
C6 C5 C8 O2 -6.1(2)
C4 C5 C8 C9 -6.9(2)
C6 C5 C8 C9 174.41(13)
C10 N1 C9 C8 171.21(13)
O2 C8 C9 N1 -2.85(19)
C5 C8 C9 N1 176.60(12)
C9 N1 C10 O3 0.7(2)
C9 N1 C10 C11 -178.47(13)
O3 C10 C11 C16 -158.42(14)
N1 C10 C11 C16 20.7(2)
O3 C10 C11 C12 19.0(2)
N1 C10 C11 C12 -161.91(13)
C16 C11 C12 C13 0.8(2)
C10 C11 C12 C13 -176.77(14)
C11 C12 C13 C14 1.3(2)
C17 O4 C14 C13 178.45(13)
C17 O4 C14 C15 -1.1(2)
C12 C13 C14 O4 178.24(13)
C12 C13 C14 C15 -2.2(2)
O4 C14 C15 C16 -179.47(13)
C13 C14 C15 C16 1.0(2)
C12 C11 C16 C15 -2.0(2)
C10 C11 C16 C15 175.38(13)
C14 C15 C16 C11 1.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 13404048
