#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/58/7155828.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_7155828
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         'C9 H9 N3 O2'
_chemical_formula_sum            'C9 H9 N3 O2'
_chemical_formula_weight         191.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_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                 101.091(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8441(3)
_cell_length_b                   14.0818(11)
_cell_length_c                   8.2393(7)
_cell_measurement_reflns_used    2635
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.82
_cell_measurement_theta_min      3.17
_cell_volume                     437.68(6)
_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 0.994
_diffrn_measured_fraction_theta_max 0.992
_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  0.0421
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6675
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        27.706
_diffrn_reflns_theta_max         29.952
_diffrn_reflns_theta_min         3.154
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_correction_T_min  0.9898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2012/1 (Sheldrick)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       plate
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0365
_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)+(0.0378P)²+0.0806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                1639
_reflns_number_total             1900
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ob01731f2.cif
_cod_data_source_block           1
_cod_database_code               7155828
_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   0.990
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_xyz
'x, y, z'
'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
O1 O 0.4993(7) 0.40603(13) 0.4143(3) 0.0364(5) Uani 1 1 d . .
O2 O 0.7383(5) 0.03224(13) 0.0212(2) 0.0268(5) Uani 1 1 d . .
N1 N 0.5770(8) 0.56764(17) 0.2700(3) 0.0359(7) Uani 1 1 d . .
N2 N 0.6239(7) 0.64408(18) 0.2029(3) 0.0309(6) Uani 1 1 d . .
N3 N 0.6532(10) 0.71851(18) 0.1585(4) 0.0422(7) Uani 1 1 d . .
C1 C 0.6259(7) 0.30133(18) 0.2101(3) 0.0223(6) Uani 1 1 d . .
C2 C 0.5639(7) 0.22171(19) 0.3006(3) 0.0248(7) Uani 1 1 d . .
H2 H 0.4986 0.2301 0.4052 0.030 Uiso 1 1 calc R U
C3 C 0.5951(8) 0.1309(2) 0.2419(3) 0.0236(6) Uani 1 1 d . .
H3 H 0.5493 0.0774 0.3048 0.028 Uiso 1 1 calc R U
C4 C 0.6945(7) 0.11847(18) 0.0894(3) 0.0218(6) Uani 1 1 d . .
C5 C 0.7571(8) 0.1972(2) -0.0034(3) 0.0250(7) Uani 1 1 d . .
H5 H 0.8233 0.1887 -0.1077 0.030 Uiso 1 1 calc R U
C6 C 0.7227(9) 0.2875(2) 0.0563(4) 0.0247(6) Uani 1 1 d . .
H6 H 0.7652 0.3409 -0.0075 0.030 Uiso 1 1 calc R U
C7 C 0.5832(8) 0.39655(19) 0.2796(4) 0.0251(6) Uani 1 1 d . .
C8 C 0.6378(9) 0.48233(18) 0.1778(4) 0.0276(7) Uani 1 1 d . .
H8A H 0.8823 0.4826 0.1561 0.033 Uiso 1 1 calc R U
H8B H 0.4703 0.4807 0.0703 0.033 Uiso 1 1 calc R U
C9 C 0.6698(9) -0.0502(2) 0.1117(4) 0.0291(7) Uani 1 1 d . .
H9A H 0.7055 -0.1074 0.0491 0.044 Uiso 1 1 calc R U
H9B H 0.4246 -0.0484 0.1290 0.044 Uiso 1 1 calc R U
H9C H 0.8323 -0.0513 0.2191 0.044 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
C4 O2 C9 117.3(2)
N2 N1 C8 115.4(2)
N3 N2 N1 171.3(3)
C2 C1 C6 118.4(2)
C2 C1 C7 118.6(2)
C6 C1 C7 123.0(2)
C3 C2 C1 121.5(2)
C2 C3 C4 119.4(3)
O2 C4 C3 124.2(2)
O2 C4 C5 115.8(2)
C3 C4 C5 120.1(3)
C6 C5 C4 120.0(2)
C5 C6 C1 120.7(2)
O1 C7 C1 121.3(2)
O1 C7 C8 120.5(2)
C1 C7 C8 118.2(2)
N1 C8 C7 108.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.221(4)
O2 C4 1.362(3)
O2 C9 1.431(3)
N1 N2 1.239(3)
N1 C8 1.464(4)
N2 N3 1.123(3)
C1 C2 1.392(3)
C1 C6 1.401(4)
C1 C7 1.479(4)
C2 C3 1.381(3)
C3 C4 1.393(4)
C4 C5 1.394(4)
C5 C6 1.378(4)
C7 C8 1.508(4)
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
C6 C1 C2 C3 -0.2(4)
C7 C1 C2 C3 179.2(3)
C1 C2 C3 C4 0.7(4)
C9 O2 C4 C3 1.4(4)
C9 O2 C4 C5 -178.8(2)
C2 C3 C4 O2 179.0(3)
C2 C3 C4 C5 -0.8(4)
O2 C4 C5 C6 -179.4(3)
C3 C4 C5 C6 0.4(5)
C4 C5 C6 C1 0.1(4)
C2 C1 C6 C5 -0.3(4)
C7 C1 C6 C5 -179.6(3)
C2 C1 C7 O1 0.8(4)
C6 C1 C7 O1 -179.8(3)
C2 C1 C7 C8 -177.8(3)
C6 C1 C7 C8 1.6(4)
N2 N1 C8 C7 177.8(3)
O1 C7 C8 N1 0.6(4)
C1 C7 C8 N1 179.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10997835
