#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:02:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180462 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/31/7213180.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_7213180
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 H20 Cl N O2'
_chemical_formula_weight         317.80
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 105.06(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.941(4)
_cell_length_b                   12.749(4)
_cell_length_c                   15.113(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.6
_cell_measurement_theta_min      12.3
_cell_volume                     1663.5(10)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3121
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0534
_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)+(0.0518P)²+0.8440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1483
_reflns_number_gt                1631
_reflns_number_total             2925
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            a905445fsup1.cif
_cod_data_source_block           j1404n=6a/6s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.8440P] 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^)+(0.0518P)^2^+0.8440P] 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        1663.5(9)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7213180
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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 1.12195(13) 0.66047(13) 1.10606(10) 0.1455(7) Uani 1 d .
O1A O 0.3126(5) 1.0360(4) 0.8258(3) 0.0530(12) Uiso 0.50 d P
O1B O 0.3668(6) 1.0458(4) 0.8628(3) 0.0598(13) Uiso 0.50 d P
O4 O 0.4950(2) 0.74716(15) 0.75945(14) 0.0584(6) Uani 1 d .
N10 N 0.5083(3) 0.91030(17) 0.83662(16) 0.0460(6) Uani 1 d .
C1 C 0.3824(4) 0.9497(3) 0.8572(3) 0.0735(11) Uani 1 d .
C2B C 0.2739(10) 0.8593(7) 0.8719(6) 0.059(2) Uani 0.50 d P
H2B H 0.1915 0.8487 0.8155 0.071 Uiso 0.50 calc PR
C2A C 0.3392(9) 0.8696(7) 0.9227(6) 0.054(2) Uani 0.50 d P
H2A H 0.3930 0.8819 0.9871 0.065 Uiso 0.50 calc PR
C3 C 0.3845(4) 0.7679(3) 0.8861(3) 0.0650(10) Uani 1 d .
H3A H 0.417(5) 0.728(3) 0.940(3) 0.113(15) Uiso 1 d .
H3B H 0.312(5) 0.730(4) 0.840(3) 0.124(18) Uiso 1 d .
C3A C 0.5215(3) 0.7958(2) 0.8469(2) 0.0474(7) Uani 1 d .
C5 C 0.5836(5) 0.7914(3) 0.7015(2) 0.0609(9) Uani 1 d .
H5A H 0.555(3) 0.754(3) 0.645(2) 0.073 Uiso 1 d .
H5B H 0.698(4) 0.783(3) 0.730(2) 0.073 Uiso 1 d .
C5A C 0.5456(4) 0.9070(3) 0.6840(2) 0.0542(8) Uani 1 d .
H5A1 H 0.436(4) 0.915(2) 0.661(2) 0.065 Uiso 1 d .
C6 C 0.6252(5) 0.9550(3) 0.6157(2) 0.0692(10) Uani 1 d .
H6A H 0.630(4) 0.901(3) 0.567(2) 0.083 Uiso 1 d .
H6B H 0.557(4) 1.009(3) 0.583(2) 0.083 Uiso 1 d .
C7 C 0.7821(5) 0.9949(3) 0.6572(3) 0.0755(11) Uani 1 d .
H7 H 0.8439 1.0114 0.6183 0.091 Uiso 1 calc R
C8 C 0.8407(4) 1.0088(3) 0.7453(3) 0.0701(10) Uani 1 d .
H8 H 0.9387 1.0386 0.7650 0.084 Uiso 1 calc R
C9A C 0.5853(3) 0.9650(2) 0.7750(2) 0.0464(7) Uani 1 d .
H9A H 0.546(3) 1.025(2) 0.766(2) 0.056 Uiso 1 d .
C9 C 0.7583(4) 0.9792(3) 0.8156(2) 0.0595(9) Uani 1 d .
H9B H 0.773(4) 1.028(3) 0.862(2) 0.071 Uiso 1 d .
H9C H 0.803(3) 0.909(3) 0.844(2) 0.071 Uiso 1 d .
C18A C 0.1580(9) 0.8789(6) 0.9029(6) 0.075(2) Uiso 0.50 d P
H18A H 0.1119 0.8690 0.8386 0.090 Uiso 0.50 calc PR
H18B H 0.1314 0.9471 0.9210 0.090 Uiso 0.50 calc PR
H18C H 0.1203 0.8262 0.9370 0.090 Uiso 0.50 calc PR
C18B C 0.2035(10) 0.8880(6) 0.9485(6) 0.075(2) Uiso 0.50 d P
H18D H 0.1351 0.8331 0.9569 0.090 Uiso 0.50 calc PR
H18E H 0.1462 0.9522 0.9337 0.090 Uiso 0.50 calc PR
H18F H 0.2841 0.8972 1.0040 0.090 Uiso 0.50 calc PR
C12 C 0.6746(3) 0.7614(2) 0.9104(2) 0.0480(7) Uani 1 d .
C13 C 0.7340(4) 0.8140(3) 0.9929(2) 0.0598(9) Uani 1 d .
H13 H 0.6812 0.8716 1.0075 0.072 Uiso 1 calc R
C14 C 0.8697(5) 0.7817(3) 1.0530(2) 0.0793(11) Uani 1 d .
H14 H 0.9082 0.8171 1.1080 0.095 Uiso 1 calc R
C15 C 0.9473(4) 0.6973(4) 1.0314(3) 0.0811(12) Uani 1 d .
C16 C 0.8903(4) 0.6429(3) 0.9522(3) 0.0783(11) Uani 1 d .
H16 H 0.9433 0.5847 0.9388 0.094 Uiso 1 calc R
C17 C 0.7535(4) 0.6744(2) 0.8918(2) 0.0592(8) Uani 1 d .
H17 H 0.7142 0.6368 0.8381 0.071 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 114.1(2) y
C1 N10 C3A 113.4(2) y
C1 N10 C9A 121.9(2) y
C3A N10 C9A 120.0(2) y
O1B C1 O1A 29.6(3) y
O1B C1 N10 120.2(4) y
O1A C1 N10 126.0(3) y
O1B C1 C2A 124.1(5) y
O1A C1 C2A 128.5(4) y
N10 C1 C2A 105.5(4) y
O1B C1 C2B 129.5(4) y
O1A C1 C2B 115.0(5) y
N10 C1 C2B 110.3(4) y
C2A C1 C2B 31.7(3) ?
C18B C2B C3 118.0(7) ?
C18B C2B C1 109.3(6) ?
C3 C2B C1 100.5(5) ?
C18B C2B H2B 109.5 ?
C3 C2B H2B 109.5 ?
C1 C2B H2B 109.5 ?
C3 C2A C1 101.4(5) ?
C3 C2A C18A 110.9(6) ?
C1 C2A C18A 104.2(6) ?
C3 C2A H2A 113.1 ?
C1 C2A H2A 113.1 ?
C18A C2A H2A 113.1 ?
C2A C3 C2B 32.6(3) ?
C2A C3 C3A 105.1(4) ?
C2B C3 C3A 109.0(4) ?
C2A C3 H3A 102(3) ?
C2B C3 H3A 126(3) ?
C3A C3 H3A 111(3) ?
C2A C3 H3B 121(3) ?
C2B C3 H3B 90(3) ?
C3A C3 H3B 107(3) ?
H3A C3 H3B 111(4) ?
O4 C3A N10 110.2(2) ?
O4 C3A C12 111.5(2) ?
N10 C3A C12 112.9(2) ?
O4 C3A C3 107.5(3) ?
N10 C3A C3 102.8(2) ?
C12 C3A C3 111.6(3) ?
O4 C5 C5A 110.6(3) ?
O4 C5 H5A 107(2) ?
C5A C5 H5A 109.6(19) ?
O4 C5 H5B 110.5(18) ?
C5A C5 H5B 109.7(19) ?
H5A C5 H5B 110(3) ?
C9A C5A C5 109.0(3) ?
C9A C5A C6 112.1(3) ?
C5 C5A C6 112.6(3) ?
C9A C5A H5A1 104.7(18) ?
C5 C5A H5A1 109.2(19) ?
C6 C5A H5A1 108.9(18) ?
C7 C6 C5A 114.2(3) ?
C7 C6 H6A 109.3(19) ?
C5A C6 H6A 109.2(19) ?
C7 C6 H6B 112(2) ?
C5A C6 H6B 107(2) ?
H6A C6 H6B 104(3) ?
C8 C7 C6 124.5(3) ?
C8 C7 H7 117.8 ?
C6 C7 H7 117.8 ?
C7 C8 C9 123.3(3) ?
C7 C8 H8 118.4 ?
C9 C8 H8 118.4 ?
N10 C9A C9 113.3(2) ?
N10 C9A C5A 107.7(2) ?
C9 C9A C5A 113.4(3) ?
N10 C9A H9A 107(2) ?
C9 C9A H9A 107(2) ?
C5A C9A H9A 108(2) ?
C8 C9 C9A 112.5(3) ?
C8 C9 H9B 112(2) ?
C9A C9 H9B 108(2) ?
C8 C9 H9C 107.9(18) ?
C9A C9 H9C 107.8(18) ?
H9B C9 H9C 108(3) ?
C2A C18A H18A 109.5 ?
C2A C18A H18B 109.5 ?
H18A C18A H18B 109.5 ?
C2A C18A H18C 109.5 ?
H18A C18A H18C 109.5 ?
H18B C18A H18C 109.5 ?
C2B C18B H18D 109.5 ?
C2B C18B H18E 109.5 ?
H18D C18B H18E 109.5 ?
C2B C18B H18F 109.5 ?
H18D C18B H18F 109.5 ?
H18E C18B H18F 109.5 ?
C17 C12 C13 118.2(3) ?
C17 C12 C3A 121.8(3) ?
C13 C12 C3A 119.9(3) ?
C14 C13 C12 120.8(3) ?
C14 C13 H13 119.6 ?
C12 C13 H13 119.6 ?
C15 C14 C13 119.5(4) ?
C15 C14 H14 120.2 ?
C13 C14 H14 120.2 ?
C16 C15 C14 121.0(4) ?
C16 C15 Cl 120.1(4) ?
C14 C15 Cl 119.0(4) ?
C15 C16 C17 119.8(4) ?
C15 C16 H16 120.1 ?
C17 C16 H16 120.1 ?
C12 C17 C16 120.7(3) ?
C12 C17 H17 119.7 ?
C16 C17 H17 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C15 1.737(4) y
O1A C1 1.293(5) y
O1B C1 1.239(5) y
O4 C3A 1.423(3) y
O4 C5 1.440(4) y
N10 C1 1.341(4) y
N10 C3A 1.470(3) y
N10 C9A 1.471(3) y
C1 C2A 1.540(9) ?
C1 C2B 1.559(9) ?
C2B C18B 1.501(11) ?
C2B C3 1.508(9) ?
C2B H2B 0.9800 ?
C2A C3 1.507(9) ?
C2A C18A 1.573(10) ?
C2A H2A 0.9800 ?
C3 C3A 1.535(4) ?
C3 H3A 0.94(4) ?
C3 H3B 0.94(4) ?
C3A C12 1.518(4) ?
C5 C5A 1.520(4) ?
C5 H5A 0.95(3) ?
C5 H5B 1.01(3) ?
C5A C9A 1.519(4) ?
C5A C6 1.527(5) ?
C5A H5A1 0.96(3) ?
C6 C7 1.470(5) ?
C6 H6A 1.01(4) ?
C6 H6B 0.97(3) ?
C7 C8 1.310(5) ?
C7 H7 0.9300 ?
C8 C9 1.490(4) ?
C8 H8 0.9300 ?
C9A C9 1.519(4) ?
C9A H9A 0.84(3) ?
C9 H9B 0.93(3) ?
C9 H9C 1.03(3) ?
C18A H18A 0.9600 ?
C18A H18B 0.9600 ?
C18A H18C 0.9600 ?
C18B H18D 0.9600 ?
C18B H18E 0.9600 ?
C18B H18F 0.9600 ?
C12 C17 1.381(4) ?
C12 C13 1.394(4) ?
C13 C14 1.377(5) ?
C13 H13 0.9300 ?
C14 C15 1.366(5) ?
C14 H14 0.9300 ?
C15 C16 1.362(5) ?
C16 C17 1.383(5) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
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
C17 H17 O4 0.93 2.45 2.792(4) 101.5
C13 H13 N10 0.93 2.69 2.946(4) 96.8
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 O1B 170.9(4)
C9A N10 C1 O1B -33.4(6)
C3A N10 C1 O1A -154.3(4)
C9A N10 C1 O1A 1.4(6)
C3A N10 C1 C2A 24.4(5)
C9A N10 C1 C2A -179.9(4)
C3A N10 C1 C2B -8.6(5)
C9A N10 C1 C2B 147.1(4)
O1B C1 C2B C18B -37.0(10)
O1A C1 C2B C18B -67.8(8)
N10 C1 C2B C18B 142.4(6)
C2A C1 C2B C18B 55.7(9)
O1B C1 C2B C3 -161.8(5)
O1A C1 C2B C3 167.4(5)
N10 C1 C2B C3 17.6(7)
C2A C1 C2B C3 -69.1(9)
O1B C1 C2A C3 -178.9(5)
O1A C1 C2A C3 144.6(5)
N10 C1 C2A C3 -34.0(6)
C2B C1 C2A C3 69.7(9)
O1B C1 C2A C18A 65.9(8)
O1A C1 C2A C18A 29.3(9)
N10 C1 C2A C18A -149.3(5)
C2B C1 C2A C18A -45.6(8)
C1 C2A C3 C2B -70.9(9)
C18A C2A C3 C2B 39.3(8)
C1 C2A C3 C3A 30.9(6)
C18A C2A C3 C3A 141.1(6)
C18B C2B C3 C2A -50.1(9)
C1 C2B C3 C2A 68.5(9)
C18B C2B C3 C3A -138.6(7)
C1 C2B C3 C3A -19.9(7)
C5 O4 C3A N10 49.8(3)
C5 O4 C3A C12 -76.3(3)
C5 O4 C3A C3 161.1(3)
C1 N10 C3A O4 110.0(3)
C9A N10 C3A O4 -46.2(3)
C1 N10 C3A C12 -124.6(3)
C9A N10 C3A C12 79.1(3)
C1 N10 C3A C3 -4.3(4)
C9A N10 C3A C3 -160.5(3)
C2A C3 C3A O4 -134.2(4)
C2B C3 C3A O4 -100.3(5)
C2A C3 C3A N10 -18.0(5)
C2B C3 C3A N10 15.9(6)
C2A C3 C3A C12 103.2(5)
C2B C3 C3A C12 137.1(5)
C3A O4 C5 C5A -59.8(3)
O4 C5 C5A C9A 60.4(4)
O4 C5 C5A C6 -174.6(3)
C9A C5A C6 C7 36.2(4)
C5 C5A C6 C7 -87.2(4)
C5A C6 C7 C8 -13.1(6)
C6 C7 C8 C9 4.0(6)
C1 N10 C9A C9 128.1(3)
C3A N10 C9A C9 -77.8(3)
C1 N10 C9A C5A -105.7(3)
C3A N10 C9A C5A 48.5(3)
C5 C5A C9A N10 -52.4(3)
C6 C5A C9A N10 -177.8(3)
C5 C5A C9A C9 73.7(4)
C6 C5A C9A C9 -51.6(4)
C7 C8 C9 C9A -18.4(5)
N10 C9A C9 C8 165.1(3)
C5A C9A C9 C8 42.0(4)
O4 C3A C12 C17 -15.6(4)
N10 C3A C12 C17 -140.3(3)
C3 C3A C12 C17 104.6(3)
O4 C3A C12 C13 168.6(2)
N10 C3A C12 C13 44.0(4)
C3 C3A C12 C13 -71.1(4)
C17 C12 C13 C14 1.7(5)
C3A C12 C13 C14 177.6(3)
C12 C13 C14 C15 0.2(5)
C13 C14 C15 C16 -1.7(6)
C13 C14 C15 Cl 177.7(3)
C14 C15 C16 C17 1.3(6)
Cl C15 C16 C17 -178.1(3)
C13 C12 C17 C16 -2.1(4)
C3A C12 C17 C16 -178.0(3)
C15 C16 C17 C12 0.7(5)
