#------------------------------------------------------------------------------
#$Date: 2021-10-14 05:28:04 +0300 (Thu, 14 Oct 2021) $
#$Revision: 269937 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/39/2243934.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_2243934
loop_
_publ_author_name
'Poirot, Alexandre'
'Saffon-Merceron, Nathalie'
'Leygue, Nadine'
'Benoist, Eric'
'Fery-Forgues, Suzanne'
_publ_section_title
;
 Crystal structure of methyl 1,3-benzoxazole-2-carboxylate
;
_journal_coeditor_code           DJ2033
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989021010094
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C9 H7 N O3'
_chemical_formula_moiety         'C9 H7 N O3'
_chemical_formula_sum            'C9 H7 N O3'
_chemical_formula_weight         177.16
_chemical_name_systematic
;
Methyl 1,3-benzoxazole-2-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 95.1319(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8165(3)
_cell_length_b                   4.4676(2)
_cell_length_c                   13.2879(6)
_cell_measurement_reflns_used    6695
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      3.25
_cell_volume                     403.04(3)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al,
2020)
;
_computing_publication_material
;
Platon (Spek 2020) and publCIF (Westrip 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8-Venture Photon III detector'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9084
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_min         3.248
_diffrn_source                   'Fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       plate
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1954
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0299
_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)+(0.0432P)²+0.0403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                1860
_reflns_number_total             1954
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dj2033sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2243934
_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   0.957
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 0.25255(16) 0.3885(3) 0.69933(9) 0.0329(3) Uani d 1 . .
O O2 0.43981(19) -0.0004(3) 0.57993(9) 0.0382(3) Uani d 1 . .
O O3 0.73220(17) 0.2017(3) 0.63833(9) 0.0341(3) Uani d 1 . .
N N1 0.54541(19) 0.5493(3) 0.77177(10) 0.0277(3) Uani d 1 . .
C C1 0.4528(2) 0.3789(4) 0.70473(12) 0.0296(3) Uani d 1 . .
C C2 0.5378(2) 0.1703(4) 0.63294(12) 0.0297(3) Uani d 1 . .
C C3 0.8319(3) 0.0125(4) 0.57015(13) 0.0381(4) Uani d 1 . .
H H3A 0.794777 -0.196824 0.579791 0.057 Uiso calc 1 . .
H H3B 0.974729 0.034297 0.584461 0.057 Uiso calc 1 . .
H H3C 0.793506 0.072127 0.500188 0.057 Uiso calc 1 . .
C C4 0.2149(2) 0.5919(4) 0.77264(12) 0.0291(3) Uani d 1 . .
C C5 0.3947(2) 0.6919(4) 0.81779(11) 0.0273(3) Uani d 1 . .
C C6 0.4014(2) 0.9009(4) 0.89607(13) 0.0347(4) Uani d 1 . .
H H6 0.522730 0.971603 0.928121 0.042 Uiso calc 1 . .
C C7 0.2220(3) 0.9998(4) 0.92465(14) 0.0401(4) Uani d 1 . .
H H7 0.220300 1.141802 0.977785 0.048 Uiso calc 1 . .
C C8 0.0429(3) 0.8959(5) 0.87719(15) 0.0406(4) Uani d 1 . .
H H8 -0.076652 0.971435 0.898830 0.049 Uiso calc 1 . .
C C9 0.0342(2) 0.6878(5) 0.80018(14) 0.0370(4) Uani d 1 . .
H H9 -0.087048 0.615698 0.768384 0.044 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
C1 O1 C4 . . 103.51(12) ?
C2 O3 C3 . . 115.17(14) ?
C1 N1 C5 . . 103.74(13) ?
N1 C1 O1 . . 116.33(15) ?
N1 C1 C2 . . 128.06(14) ?
O1 C1 C2 . . 115.61(13) ?
O2 C2 O3 . . 126.82(17) ?
O2 C2 C1 . . 123.11(16) ?
O3 C2 C1 . . 110.07(14) ?
O3 C3 H3A . . 109.5 ?
O3 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
O3 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O1 C4 C9 . . 128.30(15) ?
O1 C4 C5 . . 107.78(14) ?
C9 C4 C5 . . 123.92(17) ?
C4 C5 N1 . . 108.64(15) ?
C4 C5 C6 . . 120.36(15) ?
N1 C5 C6 . . 131.00(14) ?
C7 C6 C5 . . 116.58(16) ?
C7 C6 H6 . . 121.7 ?
C5 C6 H6 . . 121.7 ?
C6 C7 C8 . . 121.71(18) ?
C6 C7 H7 . . 119.1 ?
C8 C7 H7 . . 119.1 ?
C9 C8 C7 . . 122.32(17) ?
C9 C8 H8 . . 118.8 ?
C7 C8 H8 . . 118.8 ?
C8 C9 C4 . . 115.10(16) ?
C8 C9 H9 . . 122.4 ?
C4 C9 H9 . . 122.4 ?
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 C1 . 1.3610(19) ?
O1 C4 . 1.373(2) ?
O2 C2 . 1.200(2) ?
O3 C2 . 1.3281(19) ?
O3 C3 . 1.452(2) ?
N1 C1 . 1.293(2) ?
N1 C5 . 1.395(2) ?
C1 C2 . 1.488(2) ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C4 C9 . 1.384(2) ?
C4 C5 . 1.390(2) ?
C5 C6 . 1.395(2) ?
C6 C7 . 1.385(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.402(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.380(3) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
C9 H9 N1 1_555 1_555 1_455 0.95 2.53 3.377(2) 149 yes
C3 H3C O2 1_555 1_555 2_656 0.98 2.65 3.389(2) 133 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
C5 N1 C1 O1 . . . . 0.05(19) ?
C5 N1 C1 C2 . . . . -179.34(15) ?
C4 O1 C1 N1 . . . . 0.03(18) ?
C4 O1 C1 C2 . . . . 179.50(13) ?
C3 O3 C2 O2 . . . . 1.7(2) ?
C3 O3 C2 C1 . . . . -178.99(13) ?
N1 C1 C2 O2 . . . . 172.61(18) ?
O1 C1 C2 O2 . . . . -6.8(2) ?
N1 C1 C2 O3 . . . . -6.7(2) ?
O1 C1 C2 O3 . . . . 173.92(14) ?
C1 O1 C4 C9 . . . . -179.89(17) ?
C1 O1 C4 C5 . . . . -0.10(16) ?
O1 C4 C5 N1 . . . . 0.14(17) ?
C9 C4 C5 N1 . . . . 179.93(15) ?
O1 C4 C5 C6 . . . . -179.61(14) ?
C9 C4 C5 C6 . . . . 0.2(2) ?
C1 N1 C5 C4 . . . . -0.11(17) ?
C1 N1 C5 C6 . . . . 179.60(17) ?
C4 C5 C6 C7 . . . . -0.2(2) ?
N1 C5 C6 C7 . . . . -179.92(16) ?
C5 C6 C7 C8 . . . . -0.1(3) ?
C6 C7 C8 C9 . . . . 0.6(3) ?
C7 C8 C9 C4 . . . . -0.6(3) ?
O1 C4 C9 C8 . . . . 180.00(16) ?
C5 C4 C9 C8 . . . . 0.2(3) ?

_cod_database_fobs_code 2243934
