#------------------------------------------------------------------------------
#$Date: 2019-11-11 20:12:39 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227221 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/57/4035789.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4035789
loop_
_publ_author_name
'Das, Malay'
'Saikia, Anil K.'
_publ_section_title
;
 Stereoselective Synthesis of Pyrroloisoindolone and Pyridoisoindolone via
 aza-Prins Cyclization of Endocyclic N-Acyliminium Ions.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6178
_journal_page_last               6185
_journal_paper_doi               10.1021/acs.joc.8b00440
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C18 H14 Cl N O2'
_chemical_formula_weight         311.75
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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                 92.941(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1429(7)
_cell_length_b                   7.2183(4)
_cell_length_c                   17.3189(11)
_cell_measurement_reflns_used    2461
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.39
_cell_measurement_theta_min      2.36
_cell_volume                     1516.02(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16059
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0100P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0787
_reflns_number_gt                1701
_reflns_number_total             2681
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00440_si_003.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4035789
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl -0.11359(6) 0.98877(11) 0.13392(5) 0.1082(3) Uani 1 1 d .
O2 O 0.18113(14) 0.2163(2) 0.17102(10) 0.0872(6) Uani 1 1 d .
O1 O 0.61441(12) 0.2593(2) -0.01082(9) 0.0670(4) Uani 1 1 d .
N1 N 0.44124(14) 0.1953(2) 0.02902(9) 0.0498(4) Uani 1 1 d .
C15 C 0.0695(2) 0.8191(3) 0.08935(14) 0.0708(7) Uani 1 1 d .
H15 H 0.0848 0.9285 0.0637 0.085 Uiso 1 1 calc R
C14 C -0.0241(2) 0.8023(4) 0.12934(15) 0.0716(7) Uani 1 1 d .
C13 C -0.0494(2) 0.6418(4) 0.16697(14) 0.0766(8) Uani 1 1 d .
H13 H -0.1142 0.6326 0.1931 0.092 Uiso 1 1 calc R
C12 C 0.02269(18) 0.4943(4) 0.16542(12) 0.0661(7) Uani 1 1 d .
H12 H 0.0063 0.3848 0.1907 0.079 Uiso 1 1 calc R
C11 C 0.11945(16) 0.5078(3) 0.12644(12) 0.0528(6) Uani 1 1 d .
C16 C 0.14095(18) 0.6706(3) 0.08784(13) 0.0623(6) Uani 1 1 d .
H16 H 0.2046 0.6801 0.0604 0.075 Uiso 1 1 calc R
C5 C 0.5672(2) 0.2715(3) 0.28252(14) 0.0689(7) Uani 1 1 d .
H5 H 0.5671 0.2777 0.3362 0.083 Uiso 1 1 calc R
C6 C 0.46929(19) 0.2431(3) 0.24031(12) 0.0587(6) Uani 1 1 d .
H6 H 0.4033 0.2303 0.2647 0.070 Uiso 1 1 calc R
C3 C 0.66899(18) 0.2807(3) 0.16738(14) 0.0650(6) Uani 1 1 d .
H3 H 0.7350 0.2939 0.1430 0.078 Uiso 1 1 calc R
C2 C 0.57059(17) 0.2498(3) 0.12519(12) 0.0505(5) Uani 1 1 d .
C7 C 0.47188(16) 0.2341(3) 0.16081(11) 0.0474(5) Uani 1 1 d .
C10 C 0.19775(17) 0.3493(3) 0.13048(13) 0.0564(6) Uani 1 1 d .
C9 C 0.29691(15) 0.3546(3) 0.08183(11) 0.0471(5) Uani 1 1 d .
H9 H 0.3327 0.4759 0.0873 0.057 Uiso 1 1 calc R
C17 C 0.26616(17) 0.3180(3) -0.00414(12) 0.0622(6) Uani 1 1 d .
H17A H 0.2087 0.2250 -0.0098 0.075 Uiso 1 1 calc R
H17B H 0.2405 0.4308 -0.0297 0.075 Uiso 1 1 calc R
C18 C 0.37238(17) 0.2493(3) -0.03847(12) 0.0604(6) Uani 1 1 d .
H18A H 0.3579 0.1445 -0.0726 0.073 Uiso 1 1 calc R
H18B H 0.4070 0.3469 -0.0671 0.073 Uiso 1 1 calc R
C1 C 0.54952(18) 0.2361(3) 0.04065(13) 0.0516(5) Uani 1 1 d .
C8 C 0.38142(16) 0.2027(3) 0.10042(11) 0.0477(5) Uani 1 1 d .
H8 H 0.3444 0.0845 0.1092 0.057 Uiso 1 1 calc R
C4 C 0.6655(2) 0.2911(3) 0.24663(15) 0.0722(7) Uani 1 1 d .
H4 H 0.7302 0.3116 0.2764 0.087 Uiso 1 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'
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'
H H 0.0000 0.0000 '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
C1 N1 C18 125.14(18)
C1 N1 C8 112.71(17)
C18 N1 C8 112.23(15)
C14 C15 C16 118.7(2)
C14 C15 H15 120.6
C16 C15 H15 120.6
C15 C14 C13 121.9(2)
C15 C14 Cl1 119.6(2)
C13 C14 Cl1 118.5(2)
C14 C13 C12 119.0(2)
C14 C13 H13 120.5
C12 C13 H13 120.5
C13 C12 C11 120.6(2)
C13 C12 H12 119.7
C11 C12 H12 119.7
C16 C11 C12 118.7(2)
C16 C11 C10 122.69(19)
C12 C11 C10 118.6(2)
C15 C16 C11 121.1(2)
C15 C16 H16 119.5
C11 C16 H16 119.5
C6 C5 C4 121.2(2)
C6 C5 H5 119.4
C4 C5 H5 119.4
C5 C6 C7 118.2(2)
C5 C6 H6 120.9
C7 C6 H6 120.9
C4 C3 C2 117.7(2)
C4 C3 H3 121.2
C2 C3 H3 121.2
C7 C2 C3 121.5(2)
C7 C2 C1 109.11(18)
C3 C2 C1 129.4(2)
C6 C7 C2 120.4(2)
C6 C7 C8 130.66(19)
C2 C7 C8 108.87(17)
O2 C10 C11 120.77(19)
O2 C10 C9 120.4(2)
C11 C10 C9 118.8(2)
C10 C9 C8 114.39(17)
C10 C9 C17 112.08(17)
C8 C9 C17 102.01(16)
C10 C9 H9 109.4
C8 C9 H9 109.4
C17 C9 H9 109.4
C18 C17 C9 105.30(16)
C18 C17 H17A 110.7
C9 C17 H17A 110.7
C18 C17 H17B 110.7
C9 C17 H17B 110.7
H17A C17 H17B 108.8
N1 C18 C17 103.64(16)
N1 C18 H18A 111.0
C17 C18 H18A 111.0
N1 C18 H18B 111.0
C17 C18 H18B 111.0
H18A C18 H18B 109.0
O1 C1 N1 125.1(2)
O1 C1 C2 128.6(2)
N1 C1 C2 106.26(18)
N1 C8 C7 102.56(15)
N1 C8 C9 101.85(15)
C7 C8 C9 120.07(17)
N1 C8 H8 110.5
C7 C8 H8 110.5
C9 C8 H8 110.5
C3 C4 C5 121.0(2)
C3 C4 H4 119.5
C5 C4 H4 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C14 1.734(2)
O2 C10 1.213(2)
O1 C1 1.231(2)
N1 C1 1.352(2)
N1 C18 1.455(3)
N1 C8 1.467(2)
C15 C14 1.367(3)
C15 C16 1.380(3)
C15 H15 0.9300
C14 C13 1.371(4)
C13 C12 1.380(3)
C13 H13 0.9300
C12 C11 1.388(3)
C12 H12 0.9300
C11 C16 1.383(3)
C11 C10 1.487(3)
C16 H16 0.9300
C5 C6 1.379(3)
C5 C4 1.381(3)
C5 H5 0.9300
C6 C7 1.380(3)
C6 H6 0.9300
C3 C4 1.377(3)
C3 C2 1.386(3)
C3 H3 0.9300
C2 C7 1.381(3)
C2 C1 1.477(3)
C7 C8 1.495(3)
C10 C9 1.505(3)
C9 C8 1.525(3)
C9 C17 1.539(3)
C9 H9 0.9800
C17 C18 1.530(3)
C17 H17A 0.9700
C17 H17B 0.9700
C18 H18A 0.9700
C18 H18B 0.9700
C8 H8 0.9800
C4 H4 0.9300
