#------------------------------------------------------------------------------
#$Date: 2023-08-16 04:47:53 +0300 (Wed, 16 Aug 2023) $
#$Revision: 285783 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022834.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_2022834
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      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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;FinalCif V117 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_cell_angle_alpha                90
_cell_angle_beta                 104.095(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6327(5)
_cell_length_b                   9.5561(6)
_cell_length_c                   11.2899(7)
_cell_measurement_reflns_used    7334
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.032
_cell_measurement_theta_min      2.752
_cell_volume                     798.68(9)
_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 1.000
_diffrn_measured_fraction_theta_max 0.991
_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  0.0585
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.408
_diffrn_reflns_theta_min         2.751
_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    0.110
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0408
_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)+(0.0404P)²+0.4603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                1496
_reflns_number_total             1988
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            eq3010sup1.cif
_cod_data_source_block           A
_cod_database_code               2022834
_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   0.983
_shelx_estimated_absorpt_t_max   0.996
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_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 0.93737(15) 0.86449(11) 0.40596(9) 0.0215(3) Uani d 1 . .
O O2 0.90744(16) 0.88984(12) 0.59702(9) 0.0220(3) Uani d 1 . .
H H2 0.962(4) 0.979(3) 0.591(2) 0.083(9) Uiso d 1 . .
N N1 0.56587(18) 0.34979(13) 0.20286(11) 0.0219(3) Uani d 1 . .
N N2 0.50663(18) 0.46363(14) 0.15900(11) 0.0208(3) Uani d 1 . .
N N3 0.4361(2) 0.56102(16) 0.11360(13) 0.0306(3) Uani d 1 . .
C C1 0.82040(18) 0.67382(14) 0.49777(12) 0.0137(3) Uani d 1 . .
C C2 0.81239(18) 0.58766(14) 0.39627(12) 0.0137(3) Uani d 1 . .
H H2A 0.845507 0.623981 0.326465 0.016 Uiso calc 1 . .
C C3 0.75637(18) 0.44948(15) 0.39698(12) 0.0140(3) Uani d 1 . .
C C4 0.70877(19) 0.39726(15) 0.50081(13) 0.0159(3) Uani d 1 . .
H H4 0.671218 0.302652 0.502454 0.019 Uiso calc 1 . .
C C5 0.71607(19) 0.48268(15) 0.60125(13) 0.0172(3) Uani d 1 . .
H H5 0.683240 0.446267 0.671121 0.021 Uiso calc 1 . .
C C6 0.77106(19) 0.62109(15) 0.60026(12) 0.0159(3) Uani d 1 . .
H H6 0.775077 0.679528 0.668945 0.019 Uiso calc 1 . .
C C7 0.89182(19) 0.81756(15) 0.49687(12) 0.0152(3) Uani d 1 . .
C C8 0.74914(19) 0.35650(15) 0.28813(12) 0.0172(3) Uani d 1 . .
H H8A 0.836393 0.391527 0.243022 0.021 Uiso calc 1 . .
H H8B 0.786820 0.260833 0.317165 0.021 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 . . 111.0(17) ?
N2 N1 C8 . . 114.49(12) ?
N3 N2 N1 . . 172.89(16) ?
C2 C1 C7 . . 118.90(12) ?
C6 C1 C2 . . 119.97(13) ?
C6 C1 C7 . . 121.03(12) ?
C1 C2 H2A . . 119.8 ?
C3 C2 C1 . . 120.44(12) ?
C3 C2 H2A . . 119.8 ?
C2 C3 C4 . . 119.11(12) ?
C2 C3 C8 . . 120.42(12) ?
C4 C3 C8 . . 120.46(12) ?
C3 C4 H4 . . 119.8 ?
C5 C4 C3 . . 120.49(13) ?
C5 C4 H4 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C4 C5 C6 . . 120.40(13) ?
C6 C5 H5 . . 119.8 ?
C1 C6 H6 . . 120.2 ?
C5 C6 C1 . . 119.59(13) ?
C5 C6 H6 . . 120.2 ?
O1 C7 O2 . . 122.59(13) ?
O1 C7 C1 . . 121.19(12) ?
O2 C7 C1 . . 116.21(12) ?
N1 C8 C3 . . 113.18(12) ?
N1 C8 H8A . . 108.9 ?
N1 C8 H8B . . 108.9 ?
C3 C8 H8A . . 108.9 ?
C3 C8 H8B . . 108.9 ?
H8A C8 H8B . . 107.8 ?
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 . 1.2446(17) ?
O2 H2 . 0.96(3) ?
O2 C7 . 1.3054(17) ?
N1 N2 . 1.2345(18) ?
N1 C8 . 1.4939(19) ?
N2 N3 . 1.1333(19) ?
C1 C2 . 1.4002(19) ?
C1 C6 . 1.3953(19) ?
C1 C7 . 1.479(2) ?
C2 H2A . 0.9500 ?
C2 C3 . 1.389(2) ?
C3 C4 . 1.4010(19) ?
C3 C8 . 1.5065(19) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.387(2) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.389(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 3_776 0.96(3) 1.68(3) 2.6334(15) 175(3) 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 . . . . 59.97(17) ?
C1 C2 C3 C4 . . . . -0.3(2) ?
C1 C2 C3 C8 . . . . -179.53(12) ?
C2 C1 C6 C5 . . . . 0.7(2) ?
C2 C1 C7 O1 . . . . 3.0(2) ?
C2 C1 C7 O2 . . . . -175.56(13) ?
C2 C3 C4 C5 . . . . 0.5(2) ?
C2 C3 C8 N1 . . . . -95.73(15) ?
C3 C4 C5 C6 . . . . -0.1(2) ?
C4 C3 C8 N1 . . . . 85.04(16) ?
C4 C5 C6 C1 . . . . -0.5(2) ?
C6 C1 C2 C3 . . . . -0.3(2) ?
C6 C1 C7 O1 . . . . 179.39(13) ?
C6 C1 C7 O2 . . . . 0.8(2) ?
C7 C1 C2 C3 . . . . 176.11(12) ?
C7 C1 C6 C5 . . . . -175.65(13) ?
C8 C3 C4 C5 . . . . 179.75(13) ?

_cod_database_fobs_code 2022834
