#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/31/7213179.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7213179
loop_
_publ_author_name
'Tähtinen, Petri'
'Sillanpää, Reijo'
'Stájer, Géza'
'Szabó, Angela E.'
'Pihlaja, Kalevi'
_publ_section_title
;
 NMR and X-ray structural study of saturated
 ( p-chlorophenyl)pyrrolo[1,2-a][3,1]benzoxazin-1-ones prepared
 from aroylisobutyric acid and cyclic amino alcohols. High energy barriers
 for hindered rotation of bridgehead phenyl groups
;
_journal_issue                   10
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              2011
_journal_paper_doi               10.1039/a905445f
_journal_year                    1999
_chemical_formula_sum            'C18 H22 Cl N O2'
_chemical_formula_weight         319.82
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.623(2)
_cell_length_b                   11.443(3)
_cell_length_c                   10.698(2)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      9.1
_cell_measurement_theta_min      6.5
_cell_volume                     3259.1(11)
_computing_cell_refinement
;
MSC/AFC5S Control Program (Molecular Structure Corporation, 1995)
;
_computing_data_collection
; 
MSC/AFC5S Control Program (Molecular Structure Corporation, 1995)
;
_computing_data_reduction
;
TEXSAN for WINDOWS(Molecular Structure Corporation, 1997)
;
_computing_molecular_graphics    'ORTEP-3 for WINDOWS (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare, 1994)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.884
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_device_type  'Rigaku AFC5S'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0932
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2875
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.0526
_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)+(0.0356P)²+0.4890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                1534
_reflns_number_total             2875
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            a905445fsup1.cif
_cod_data_source_block           j1403=5a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.4890P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.4890P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3259.2(12)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7213179
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'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_calc_flag
_atom_site_refinement_flags
Cl Cl 0.94765(4) -0.20073(8) 1.04154(9) 0.0555(3) Uani 1 d .
O1 O 0.84794(10) -0.0434(3) 0.3464(3) 0.0749(9) Uani 1 d .
O4 O 0.87640(8) 0.22721(18) 0.6505(2) 0.0455(6) Uani 1 d .
N10 N 0.85026(9) 0.0649(2) 0.5281(2) 0.0356(7) Uani 1 d .
C1 C 0.87005(14) 0.0114(3) 0.4261(4) 0.0477(10) Uani 1 d .
C2 C 0.92745(14) 0.0281(4) 0.4324(4) 0.0533(11) Uani 1 d .
H2 H 0.9410(13) -0.056(3) 0.466(3) 0.064 Uiso 1 d .
C3 C 0.93478(14) 0.1203(4) 0.5291(4) 0.0495(10) Uani 1 d .
H3A H 0.9325(12) 0.199(3) 0.487(3) 0.059 Uiso 1 d .
H3B H 0.9661(13) 0.119(3) 0.575(3) 0.059 Uiso 1 d .
C3A C 0.88855(13) 0.1126(3) 0.6123(3) 0.0370(9) Uani 1 d .
C5 C 0.82706(15) 0.2356(4) 0.7035(4) 0.0499(10) Uani 1 d .
H5A H 0.8243(13) 0.319(3) 0.726(3) 0.060 Uiso 1 d .
H5B H 0.8219(13) 0.184(3) 0.782(3) 0.060 Uiso 1 d .
C5A C 0.78732(13) 0.1974(3) 0.6111(3) 0.0412(9) Uani 1 d .
H5A1 H 0.7913(12) 0.243(3) 0.540(3) 0.049 Uiso 1 d .
C6 C 0.73463(15) 0.2096(4) 0.6634(4) 0.0527(11) Uani 1 d .
H6A H 0.7316(13) 0.162(3) 0.740(3) 0.063 Uiso 1 d .
H6B H 0.7270(13) 0.292(3) 0.689(3) 0.063 Uiso 1 d .
C7 C 0.69530(15) 0.1669(4) 0.5720(4) 0.0609(12) Uani 1 d .
H7A H 0.6641(14) 0.173(3) 0.602(3) 0.073 Uiso 1 d .
H7B H 0.6953(14) 0.218(3) 0.494(4) 0.073 Uiso 1 d .
C8 C 0.70614(15) 0.0429(4) 0.5302(5) 0.0620(12) Uani 1 d .
H8A H 0.6822(14) 0.016(3) 0.467(3) 0.074 Uiso 1 d .
H8B H 0.7047(14) -0.014(3) 0.606(4) 0.074 Uiso 1 d .
C9 C 0.75896(14) 0.0297(4) 0.4754(4) 0.0493(10) Uani 1 d .
H9A H 0.7654(13) -0.052(3) 0.450(3) 0.059 Uiso 1 d .
H9B H 0.7627(13) 0.076(3) 0.394(3) 0.059 Uiso 1 d .
C9A C 0.79772(12) 0.0712(3) 0.5700(3) 0.0373(9) Uani 1 d .
H9A1 H 0.7953(12) 0.024(3) 0.644(3) 0.045 Uiso 1 d .
C12 C 0.89783(12) 0.0329(3) 0.7255(3) 0.0338(8) Uani 1 d .
C13 C 0.88791(13) -0.0860(3) 0.7230(3) 0.0381(9) Uani 1 d .
H13 H 0.8712 -0.1179 0.6547 0.046 Uiso 1 calc R
C14 C 0.90237(12) -0.1581(3) 0.8204(3) 0.0404(9) Uani 1 d .
H14 H 0.8954 -0.2377 0.8180 0.048 Uiso 1 calc R
C15 C 0.92712(12) -0.1103(3) 0.9206(3) 0.0380(9) Uani 1 d .
C16 C 0.93629(13) 0.0081(3) 0.9278(3) 0.0457(10) Uani 1 d .
H16 H 0.9519 0.0401 0.9977 0.055 Uiso 1 calc R
C17 C 0.92190(13) 0.0785(3) 0.8291(3) 0.0438(9) Uani 1 d .
H17 H 0.9285 0.1582 0.8325 0.053 Uiso 1 calc R
C18 C 0.95019(16) 0.0473(4) 0.3034(3) 0.0687(13) Uani 1 d .
H18A H 0.9370 0.1181 0.2680 0.103 Uiso 1 calc R
H18B H 0.9419 -0.0174 0.2502 0.103 Uiso 1 calc R
H18C H 0.9860 0.0535 0.3105 0.103 Uiso 1 calc R
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C3A O4 C5 112.8(3) y
C1 N10 C3A 113.1(3) y
C1 N10 C9A 129.5(3) y
C3A N10 C9A 117.1(3) y
O1 C1 N10 127.6(3) y
O1 C1 C2 125.2(4) y
N10 C1 C2 107.1(3) y
C3 C2 C18 118.3(3) ?
C3 C2 C1 104.3(3) ?
C18 C2 C1 111.8(3) ?
C3 C2 H2 110.9(18) ?
C18 C2 H2 107.1(18) ?
C1 C2 H2 103.5(19) ?
C2 C3 C3A 105.0(3) ?
C2 C3 H3A 108.1(19) ?
C3A C3 H3A 105.4(19) ?
C2 C3 H3B 117(2) ?
C3A C3 H3B 113(2) ?
H3A C3 H3B 107(3) ?
O4 C3A N10 111.4(3) ?
O4 C3A C3 107.5(3) ?
N10 C3A C3 103.0(3) ?
O4 C3A C12 111.1(3) ?
N10 C3A C12 112.1(3) ?
C3 C3A C12 111.4(3) ?
O4 C5 C5A 111.2(3) ?
O4 C5 H5A 103(2) ?
C5A C5 H5A 113(2) ?
O4 C5 H5B 114(2) ?
C5A C5 H5B 106(2) ?
H5A C5 H5B 110(3) ?
C5 C5A C6 112.2(3) ?
C5 C5A C9A 109.5(3) ?
C6 C5A C9A 111.1(3) ?
C5 C5A H5A1 107(2) ?
C6 C5A H5A1 111(2) ?
C9A C5A H5A1 106(2) ?
C7 C6 C5A 111.8(3) ?
C7 C6 H6A 107(2) ?
C5A C6 H6A 109(2) ?
C7 C6 H6B 110(2) ?
C5A C6 H6B 112(2) ?
H6A C6 H6B 106(3) ?
C6 C7 C8 111.2(4) ?
C6 C7 H7A 113(3) ?
C8 C7 H7A 111(3) ?
C6 C7 H7B 110(2) ?
C8 C7 H7B 107(2) ?
H7A C7 H7B 105(3) ?
C7 C8 C9 112.4(3) ?
C7 C8 H8A 112(2) ?
C9 C8 H8A 108(2) ?
C7 C8 H8B 110(2) ?
C9 C8 H8B 106(2) ?
H8A C8 H8B 108(3) ?
C9A C9 C8 109.8(3) ?
C9A C9 H9A 111(2) ?
C8 C9 H9A 111(2) ?
C9A C9 H9B 110.0(19) ?
C8 C9 H9B 111.4(19) ?
H9A C9 H9B 104(3) ?
N10 C9A C9 115.3(3) ?
N10 C9A C5A 107.8(3) ?
C9 C9A C5A 111.2(3) ?
N10 C9A H9A1 106.6(19) ?
C9 C9A H9A1 109.1(19) ?
C5A C9A H9A1 106.4(19) ?
C17 C12 C13 118.3(3) ?
C17 C12 C3A 118.9(3) ?
C13 C12 C3A 122.5(3) ?
C14 C13 C12 121.2(3) ?
C14 C13 H13 119.4 ?
C12 C13 H13 119.4 ?
C15 C14 C13 119.0(3) ?
C15 C14 H14 120.5 ?
C13 C14 H14 120.5 ?
C14 C15 C16 121.3(3) ?
C14 C15 Cl 119.6(3) ?
C16 C15 Cl 119.1(3) ?
C15 C16 C17 118.8(3) ?
C15 C16 H16 120.6 ?
C17 C16 H16 120.6 ?
C16 C17 C12 121.4(3) ?
C16 C17 H17 119.3 ?
C12 C17 H17 119.3 ?
C2 C18 H18A 109.5 ?
C2 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C2 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C15 1.745(3) y
O1 C1 1.211(4) y
O4 C3A 1.412(4) y
O4 C5 1.434(4) y
N10 C1 1.358(4) y
N10 C3A 1.465(4) y
N10 C9A 1.470(4) y
C1 C2 1.541(5) ?
C2 C3 1.490(5) ?
C2 C18 1.524(5) ?
C2 H2 1.09(3) ?
C3 C3A 1.522(5) ?
C3 H3A 1.01(3) ?
C3 H3B 0.97(3) ?
C3A C12 1.536(4) ?
C5 C5A 1.513(5) ?
C5 H5A 0.99(3) ?
C5 H5B 1.04(3) ?
C5A C6 1.517(5) ?
C5A C9A 1.534(5) ?
C5A H5A1 0.93(3) ?
C6 C7 1.514(6) ?
C6 H6A 0.99(3) ?
C6 H6B 1.00(4) ?
C7 C8 1.515(6) ?
C7 H7A 0.89(4) ?
C7 H7B 1.02(4) ?
C8 C9 1.530(5) ?
C8 H8A 0.98(4) ?
C8 H8B 1.04(4) ?
C9 C9A 1.521(5) ?
C9 H9A 0.99(3) ?
C9 H9B 1.03(3) ?
C9A H9A1 0.97(3) ?
C12 C17 1.383(4) ?
C12 C13 1.387(4) ?
C13 C14 1.383(4) ?
C13 H13 0.9300 ?
C14 C15 1.372(4) ?
C14 H14 0.9300 ?
C15 C16 1.379(5) ?
C16 C17 1.382(4) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C13 H13 N10 0.93 2.55 2.887(4) 101.5
C17 H17 O4 0.93 2.52 2.831(4) 99.9
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
C3A N10 C1 O1 173.6(4)
C9A N10 C1 O1 0.1(6)
C3A N10 C1 C2 -3.7(4)
C9A N10 C1 C2 -177.2(3)
O1 C1 C2 C3 168.7(4)
N10 C1 C2 C3 -13.9(4)
O1 C1 C2 C18 39.7(6)
N10 C1 C2 C18 -143.0(3)
C18 C2 C3 C3A 150.1(3)
C1 C2 C3 C3A 25.1(4)
C5 O4 C3A N10 53.6(4)
C5 O4 C3A C3 165.7(3)
C5 O4 C3A C12 -72.1(3)
C1 N10 C3A O4 134.2(3)
C9A N10 C3A O4 -51.3(4)
C1 N10 C3A C3 19.3(4)
C9A N10 C3A C3 -166.3(3)
C1 N10 C3A C12 -100.6(3)
C9A N10 C3A C12 73.8(3)
C2 C3 C3A O4 -144.6(3)
C2 C3 C3A N10 -26.9(4)
C2 C3 C3A C12 93.4(3)
C3A O4 C5 C5A -59.4(4)
O4 C5 C5A C6 -178.0(3)
O4 C5 C5A C9A 58.2(4)
C5 C5A C6 C7 -177.9(3)
C9A C5A C6 C7 -55.0(4)
C5A C6 C7 C8 54.2(5)
C6 C7 C8 C9 -55.1(5)
C7 C8 C9 C9A 55.9(5)
C1 N10 C9A C9 -11.3(5)
C3A N10 C9A C9 175.3(3)
C1 N10 C9A C5A -136.2(3)
C3A N10 C9A C5A 50.5(4)
C8 C9 C9A N10 -179.0(3)
C8 C9 C9A C5A -56.0(4)
C5 C5A C9A N10 -52.0(4)
C6 C5A C9A N10 -176.5(3)
C5 C5A C9A C9 -179.2(3)
C6 C5A C9A C9 56.3(4)
O4 C3A C12 C17 -37.2(4)
N10 C3A C12 C17 -162.5(3)
C3 C3A C12 C17 82.6(4)
O4 C3A C12 C13 149.9(3)
N10 C3A C12 C13 24.6(4)
C3 C3A C12 C13 -90.3(4)
C17 C12 C13 C14 -1.1(5)
C3A C12 C13 C14 171.9(3)
C12 C13 C14 C15 -0.2(5)
C13 C14 C15 C16 2.1(5)
C13 C14 C15 Cl -177.7(3)
C14 C15 C16 C17 -2.7(5)
Cl C15 C16 C17 177.2(3)
C15 C16 C17 C12 1.3(5)
C13 C12 C17 C16 0.6(5)
C3A C12 C17 C16 -172.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 21629750
