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#$Date: 2023-08-16 04:47:53 +0300 (Wed, 16 Aug 2023) $
#$Revision: 285783 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022836.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022836
loop_
_publ_author_name
'Decato, Daniel'
'Jahnke, Michael'
'Berryman, Orion'
_publ_section_title
;
 Conformational polymorphism of 3-(azidomethyl)benzoic acid
;
_journal_coeditor_code           EQ3010
_journal_issue                   9
_journal_name_full
'Acta Crystallographica Section C Structural Chemistry'
_journal_paper_doi               10.1107/S2053229623006824
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C8 H7 N3 O2'
_chemical_formula_moiety         'C8 H7 N3 O2'
_chemical_formula_sum            'C8 H7 N3 O2'
_chemical_formula_weight         177.17
_chemical_name_systematic
;
3-(Azidomethyl)benzoic acid
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;FinalCif V117 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_cell_angle_alpha                66.828(2)
_cell_angle_beta                 82.168(3)
_cell_angle_gamma                82.245(2)
_cell_formula_units_Z            2
_cell_length_a                   3.8029(2)
_cell_length_b                   9.9199(5)
_cell_length_c                   11.5709(6)
_cell_measurement_reflns_used    4919
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.989
_cell_measurement_theta_min      3.468
_cell_volume                     395.96(4)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon II'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE DUO'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10604
_diffrn_reflns_theta_full        25.078
_diffrn_reflns_theta_max         25.078
_diffrn_reflns_theta_min         2.330
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       plate
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0357
_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)+(0.0480P)²+0.1860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                1196
_reflns_number_total             1405
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            eq3010sup1.cif
_cod_data_source_block           C
_cod_database_code               2022836
_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   0.966
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.0326(3) 0.83827(12) 0.49082(10) 0.0198(3) Uani d 1 . .
O O2 0.2904(3) 1.03789(12) 0.35458(11) 0.0227(3) Uani d 1 . .
H H2 0.186(6) 1.078(3) 0.410(2) 0.054(7) Uiso d 1 . .
N N1 0.3359(4) 0.40072(15) 0.21257(14) 0.0251(4) Uani d 1 . .
N N2 0.5625(4) 0.33494(15) 0.16159(13) 0.0221(3) Uani d 1 . .
N N3 0.7443(4) 0.27491(18) 0.10769(15) 0.0329(4) Uani d 1 . .
C C1 0.3888(4) 0.82269(17) 0.30991(14) 0.0161(3) Uani d 1 . .
C C2 0.3511(4) 0.67337(17) 0.34707(14) 0.0164(3) Uani d 1 . .
H H2A 0.223831 0.622462 0.425784 0.020 Uiso calc 1 . .
C C3 0.4970(4) 0.59800(17) 0.27054(14) 0.0169(3) Uani d 1 . .
C C4 0.6811(4) 0.67547(18) 0.15490(15) 0.0186(4) Uani d 1 . .
H H4 0.783049 0.625313 0.101590 0.022 Uiso calc 1 . .
C C5 0.7172(4) 0.82338(18) 0.11701(15) 0.0194(4) Uani d 1 . .
H H5 0.841506 0.874346 0.037700 0.023 Uiso calc 1 . .
C C6 0.5730(4) 0.89857(18) 0.19389(15) 0.0184(4) Uani d 1 . .
H H6 0.599376 1.000494 0.167874 0.022 Uiso calc 1 . .
C C7 0.2220(4) 0.89969(17) 0.39315(14) 0.0163(3) Uani d 1 . .
C C8 0.4606(4) 0.43609(17) 0.31271(15) 0.0199(4) Uani d 1 . .
H H8A 0.694016 0.380445 0.335739 0.024 Uiso calc 1 . .
H H8B 0.289201 0.404683 0.388834 0.024 Uiso calc 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O2 H2 . . 110.5(15) ?
N2 N1 C8 . . 115.34(13) ?
N3 N2 N1 . . 173.10(16) ?
C2 C1 C6 . . 119.94(14) ?
C2 C1 C7 . . 119.07(13) ?
C6 C1 C7 . . 120.97(13) ?
C1 C2 H2A . . 119.6 ?
C3 C2 C1 . . 120.81(14) ?
C3 C2 H2A . . 119.6 ?
C2 C3 C4 . . 118.53(14) ?
C2 C3 C8 . . 120.37(14) ?
C4 C3 C8 . . 121.10(14) ?
C3 C4 H4 . . 119.5 ?
C5 C4 C3 . . 121.01(14) ?
C5 C4 H4 . . 119.5 ?
C4 C5 H5 . . 119.8 ?
C4 C5 C6 . . 120.46(14) ?
C6 C5 H5 . . 119.8 ?
C1 C6 H6 . . 120.4 ?
C5 C6 C1 . . 119.25(15) ?
C5 C6 H6 . . 120.4 ?
O1 C7 O2 . . 122.90(14) ?
O1 C7 C1 . . 122.22(13) ?
O2 C7 C1 . . 114.88(13) ?
N1 C8 C3 . . 111.77(13) ?
N1 C8 H8A . . 109.3 ?
N1 C8 H8B . . 109.3 ?
C3 C8 H8A . . 109.3 ?
C3 C8 H8B . . 109.3 ?
H8A C8 H8B . . 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.2337(18) ?
O2 H2 . 0.90(3) ?
O2 C7 . 1.3151(19) ?
N1 N2 . 1.2364(19) ?
N1 C8 . 1.485(2) ?
N2 N3 . 1.1337(19) ?
C1 C2 . 1.392(2) ?
C1 C6 . 1.397(2) ?
C1 C7 . 1.482(2) ?
C2 H2A . 0.9500 ?
C2 C3 . 1.388(2) ?
C3 C4 . 1.397(2) ?
C3 C8 . 1.504(2) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.377(2) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.388(2) ?
C6 H6 . 0.9500 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 O1 2_576 0.90(3) 1.73(3) 2.6346(15) 176(2) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 N1 C8 C3 . . . . 108.18(15) ?
C1 C2 C3 C4 . . . . -0.4(2) ?
C1 C2 C3 C8 . . . . 178.84(13) ?
C2 C1 C6 C5 . . . . -0.1(2) ?
C2 C1 C7 O1 . . . . -4.4(2) ?
C2 C1 C7 O2 . . . . 175.81(13) ?
C2 C3 C4 C5 . . . . -0.2(2) ?
C2 C3 C8 N1 . . . . 131.44(14) ?
C3 C4 C5 C6 . . . . 0.6(2) ?
C4 C3 C8 N1 . . . . -49.36(18) ?
C4 C5 C6 C1 . . . . -0.4(2) ?
C6 C1 C2 C3 . . . . 0.5(2) ?
C6 C1 C7 O1 . . . . 173.70(14) ?
C6 C1 C7 O2 . . . . -6.1(2) ?
C7 C1 C2 C3 . . . . 178.66(13) ?
C7 C1 C6 C5 . . . . -178.22(13) ?
C8 C3 C4 C5 . . . . -179.37(14) ?

_cod_database_fobs_code 2022836
