#------------------------------------------------------------------------------
#$Date: 2019-08-23 07:15:37 +0300 (Fri, 23 Aug 2019) $
#$Revision: 217672 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/30/2243060.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_2243060
loop_
_publ_author_name
'Zreigh, Mohamed M.'
'Adams, Harry'
'Jackson, Richard F. W.'
'Robertson, Craig C.'
_publ_section_title
;
 The first crystal structure of the pyrrolo[1,2-c]oxazole ring
 system
;
_journal_coeditor_code           HB7843
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1336
_journal_page_last               1338
_journal_paper_doi               10.1107/S2056989019011095
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C7 H4 F3 N O2'
_chemical_formula_moiety         'C7 H4 F3 N O2'
_chemical_formula_sum            'C7 H4 F3 N O2'
_chemical_formula_weight         191.11
_chemical_name_systematic
;
3-Trifluoromethyl-1H-pyrrolo[1,2-c]oxazol-1-one
;
_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   geom
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.443(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2767(5)
_cell_length_b                   8.5106(5)
_cell_length_c                   10.5500(7)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      3.09
_cell_volume                     733.07(8)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            13286
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.495
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0313
_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)+(0.0348P)²+0.3122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0782
_reflns_number_gt                1595
_reflns_number_total             1681
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7843sup1.cif
_cod_data_source_block           I
_cod_database_code               2243060
_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   0.928
_shelx_estimated_absorpt_t_max   0.946
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
N N1 0.20468(11) 0.42629(11) 0.56351(8) 0.0174(2) Uani d 1
O O1 0.14217(9) 0.27976(9) 0.72729(7) 0.01878(18) Uani d 1
O O2 0.08840(11) 0.47329(9) 0.86114(7) 0.02351(19) Uani d 1
C C1 0.19006(13) 0.26514(12) 0.60398(10) 0.0173(2) Uani d 1
H H1 0.107086 0.208458 0.544158 0.021 Uiso calc 1
C C2 0.12893(12) 0.43833(12) 0.76072(10) 0.0176(2) Uani d 1
C C3 0.17020(12) 0.52963(12) 0.65500(9) 0.0168(2) Uani d 1
C C4 0.18460(13) 0.68045(13) 0.61032(10) 0.0197(2) Uani d 1
H H4 0.167818 0.773574 0.652411 0.024 Uiso calc 1
C C5 0.22998(13) 0.66468(14) 0.48775(11) 0.0221(2) Uani d 1
H H5 0.248941 0.747088 0.434193 0.027 Uiso calc 1
C C6 0.24167(14) 0.50640(14) 0.46028(10) 0.0215(2) Uani d 1
H H6 0.269396 0.463188 0.385775 0.026 Uiso calc 1
C C7 0.35527(14) 0.18148(13) 0.61947(11) 0.0211(2) Uani d 1
F F1 0.34284(9) 0.03455(8) 0.66179(7) 0.03022(19) Uani d 1
F F2 0.46888(8) 0.25554(9) 0.70256(7) 0.03067(19) Uani d 1
F F3 0.40810(8) 0.17430(9) 0.50653(7) 0.02723(18) Uani d 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 N1 C1 111.31(8)
C6 N1 C1 138.68(9)
C6 N1 C3 110.01(9)
C2 O1 C1 110.98(8)
N1 C1 H1 111.1
N1 C1 C7 110.90(9)
O1 C1 N1 103.62(8)
O1 C1 H1 111.1
O1 C1 C7 108.73(8)
C7 C1 H1 111.1
O1 C2 C3 106.55(8)
O2 C2 O1 120.33(9)
O2 C2 C3 133.12(10)
N1 C3 C2 107.54(9)
N1 C3 C4 108.48(9)
C4 C3 C2 143.96(10)
C3 C4 H4 127.0
C3 C4 C5 106.00(9)
C5 C4 H4 127.0
C4 C5 H5 125.6
C6 C5 C4 108.82(10)
C6 C5 H5 125.6
N1 C6 C5 106.68(10)
N1 C6 H6 126.7
C5 C6 H6 126.7
F1 C7 C1 110.80(9)
F2 C7 C1 111.87(9)
F2 C7 F1 107.88(9)
F2 C7 F3 108.00(9)
F3 C7 C1 110.14(9)
F3 C7 F1 108.01(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.4474(13)
N1 C3 1.3700(13)
N1 C6 1.3617(14)
O1 C1 1.4262(12)
O1 C2 1.4036(13)
O2 C2 1.2000(13)
C1 H1 0.9800
C1 C7 1.5265(15)
C2 C3 1.4456(14)
C3 C4 1.3792(15)
C4 H4 0.9300
C4 C5 1.4108(15)
C5 H5 0.9300
C5 C6 1.3846(16)
C6 H6 0.9300
C7 F1 1.3374(13)
C7 F2 1.3339(13)
C7 F3 1.3363(13)
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
C1 H1 O2 4_565 0.98 2.46 3.2683(13) 140
C6 H6 F1 4_565 0.93 2.53 3.4065(13) 156
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
N1 C1 C7 F1 177.53(8)
N1 C1 C7 F2 57.11(12)
N1 C1 C7 F3 -63.02(11)
N1 C3 C4 C5 -0.21(12)
O1 C1 C7 F1 64.22(11)
O1 C1 C7 F2 -56.21(11)
O1 C1 C7 F3 -176.33(8)
O1 C2 C3 N1 0.46(11)
O1 C2 C3 C4 178.46(14)
O2 C2 C3 N1 -178.94(11)
O2 C2 C3 C4 -0.9(2)
C1 N1 C3 C2 -0.64(11)
C1 N1 C3 C4 -179.40(8)
C1 N1 C6 C5 179.34(11)
C1 O1 C2 O2 179.38(9)
C1 O1 C2 C3 -0.12(11)
C2 O1 C1 N1 -0.25(11)
C2 O1 C1 C7 117.77(9)
C2 C3 C4 C5 -178.20(14)
C3 N1 C1 O1 0.55(11)
C3 N1 C1 C7 -115.95(9)
C3 N1 C6 C5 -0.03(12)
C3 C4 C5 C6 0.20(13)
C4 C5 C6 N1 -0.11(13)
C6 N1 C1 O1 -178.81(12)
C6 N1 C1 C7 64.69(16)
C6 N1 C3 C2 178.91(9)
C6 N1 C3 C4 0.15(12)

_cod_database_fobs_code 2243060
