#------------------------------------------------------------------------------
#$Date: 2016-04-05 22:29:44 +0300 (Tue, 05 Apr 2016) $
#$Revision: 181787 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/49/7154978.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_7154978
loop_
_publ_author_name
'Bag, Raghunath'
'Sar, Dinabandhu'
'Punniyamurthy, Tharmalingam'
_publ_section_title
;
 Iron(iii)-catalyzed aerobic dioxygenation of styrenes using
 N-hydroxyphthalimide and N-hydroxybenzotriazole.
;
_journal_issue                   12
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3246
_journal_page_last               3255
_journal_paper_doi               10.1039/c6ob00210b
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36
_chemical_name_systematic
'2-(2-hydroxy-2-phenylcyclohexyloxy)isoindoline-1,3-dione '
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-10-14 deposited with the CCDC.
2016-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.18(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.19(3)
_cell_length_b                   16.50(3)
_cell_length_c                   7.736(15)
_cell_measurement_temperature    298(2)
_cell_volume                     1777(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5583
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-Scan
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloro methane'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0449
_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)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                2404
_reflns_number_total             2990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00210b2.cif
_cod_data_source_block           ewq
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'multi-Scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154978.cif.
;
_cod_original_cell_volume        1776(6)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7154978
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
C8 C 0.33664(18) 0.51788(18) 0.0627(3) 0.0471(6) Uani 1 1 d .
C7 C 0.24675(17) 0.54129(17) -0.0624(3) 0.0466(6) Uani 1 1 d .
C1 C 0.25719(15) 0.39887(18) -0.0530(3) 0.0476(6) Uani 1 1 d .
C2 C 0.19985(17) 0.47032(17) -0.1307(3) 0.0482(7) Uani 1 1 d .
C3 C 0.11121(19) 0.4734(2) -0.2454(4) 0.0612(8) Uani 1 1 d .
H3 H 0.0796 0.4265 -0.2917 0.073 Uiso 1 1 calc R
C6 C 0.2079(2) 0.6175(2) -0.1048(4) 0.0604(7) Uani 1 1 d .
H6 H 0.2398 0.6645 -0.0597 0.073 Uiso 1 1 calc R
C4 C 0.0717(2) 0.5504(2) -0.2880(4) 0.0703(9) Uani 1 1 d .
H4 H 0.0127 0.5547 -0.3645 0.084 Uiso 1 1 calc R
C5 C 0.1186(2) 0.6203(2) -0.2186(4) 0.0696(9) Uani 1 1 d .
H5 H 0.0898 0.6703 -0.2486 0.083 Uiso 1 1 calc R
C9 C 0.52260(16) 0.28817(18) 0.2604(3) 0.0502(6) Uani 1 1 d .
C14 C 0.58474(18) 0.33977(19) 0.4041(3) 0.0537(7) Uani 1 1 d .
H14A H 0.5435 0.3750 0.4571 0.064 Uiso 1 1 calc R
H14B H 0.6187 0.3044 0.4956 0.064 Uiso 1 1 calc R
C10 C 0.47225(17) 0.34300(17) 0.1063(3) 0.0472(6) Uani 1 1 d .
H10 H 0.4396 0.3089 0.0091 0.057 Uiso 1 1 calc R
C11 C 0.54135(18) 0.3999(2) 0.0391(4) 0.0587(7) Uani 1 1 d .
H11A H 0.5047 0.4378 -0.0434 0.070 Uiso 1 1 calc R
H11B H 0.5815 0.3685 -0.0242 0.070 Uiso 1 1 calc R
C12 C 0.6056(2) 0.4474(2) 0.1851(4) 0.0649(8) Uani 1 1 d .
H12A H 0.5669 0.4860 0.2354 0.078 Uiso 1 1 calc R
H12B H 0.6527 0.4776 0.1356 0.078 Uiso 1 1 calc R
C13 C 0.65760(17) 0.39147(19) 0.3308(4) 0.0616(8) Uani 1 1 d .
H13A H 0.6948 0.4237 0.4247 0.074 Uiso 1 1 calc R
H13B H 0.7015 0.3565 0.2838 0.074 Uiso 1 1 calc R
C15 C 0.44972(18) 0.23437(19) 0.3314(4) 0.0592(7) Uani 1 1 d .
C20 C 0.4063(2) 0.1702(3) 0.2286(5) 0.0863(11) Uani 1 1 d .
H20 H 0.4205 0.1610 0.1179 0.104 Uiso 1 1 calc R
C16 C 0.4258(2) 0.2474(2) 0.4970(5) 0.0724(9) Uani 1 1 d .
H16 H 0.4537 0.2902 0.5668 0.087 Uiso 1 1 calc R
C19 C 0.3405(3) 0.1192(3) 0.2925(7) 0.1076(15) Uani 1 1 d .
H19 H 0.3119 0.0760 0.2247 0.129 Uiso 1 1 calc R
C17 C 0.3605(3) 0.1968(3) 0.5583(6) 0.0973(13) Uani 1 1 d .
H17 H 0.3456 0.2060 0.6685 0.117 Uiso 1 1 calc R
C18 C 0.3189(3) 0.1343(4) 0.4582(8) 0.1081(17) Uani 1 1 d .
H18 H 0.2754 0.1010 0.5002 0.130 Uiso 1 1 calc R
O3 O 0.39998(11) 0.38803(11) 0.1822(2) 0.0486(4) Uani 1 1 d .
O2 O 0.39499(14) 0.56004(13) 0.1564(3) 0.0631(5) Uani 1 1 d .
O4 O 0.58269(14) 0.23733(14) 0.1747(3) 0.0623(6) Uani 1 1 d .
O1 O 0.24199(13) 0.32667(14) -0.0721(3) 0.0652(5) Uani 1 1 d .
N1 N 0.33876(13) 0.43250(13) 0.0550(3) 0.0449(5) Uani 1 1 d .
H4A H 0.618(2) 0.219(2) 0.249(4) 0.056(9) Uiso 1 1 d .
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
O2 C8 N1 125.6(2)
O2 C8 C7 129.7(3)
N1 C8 C7 104.7(2)
C6 C7 C2 122.1(3)
C6 C7 C8 129.6(3)
C2 C7 C8 108.2(2)
O1 C1 N1 124.5(2)
O1 C1 C2 131.0(2)
N1 C1 C2 104.5(3)
C3 C2 C7 121.0(3)
C3 C2 C1 129.9(3)
C7 C2 C1 109.1(2)
C2 C3 C4 117.0(3)
C7 C6 C5 116.7(3)
C5 C4 C3 121.6(3)
C4 C5 C6 121.6(3)
O4 C9 C14 110.3(2)
O4 C9 C15 109.0(3)
C14 C9 C15 113.1(2)
O4 C9 C10 102.1(2)
C14 C9 C10 110.3(3)
C15 C9 C10 111.6(2)
C13 C14 C9 112.0(2)
O3 C10 C11 111.7(3)
O3 C10 C9 103.8(2)
C11 C10 C9 113.0(2)
C10 C11 C12 113.4(3)
C11 C12 C13 111.7(3)
C12 C13 C14 110.2(2)
C20 C15 C16 118.6(3)
C20 C15 C9 119.1(3)
C16 C15 C9 122.3(3)
C15 C20 C19 120.1(4)
C17 C16 C15 120.8(4)
C18 C19 C20 119.5(4)
C18 C17 C16 120.4(4)
C17 C18 C19 120.7(4)
N1 O3 C10 111.8(2)
O3 N1 C1 122.9(2)
O3 N1 C8 120.9(2)
C1 N1 C8 113.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C8 O2 1.209(4)
C8 N1 1.410(4)
C8 C7 1.495(4)
C7 C6 1.386(5)
C7 C2 1.399(4)
C1 O1 1.214(4)
C1 N1 1.404(4)
C1 C2 1.491(4)
C2 C3 1.392(4)
C3 C4 1.401(5)
C6 C5 1.397(5)
C4 C5 1.386(5)
C9 O4 1.445(4)
C9 C14 1.535(4)
C9 C15 1.542(4)
C9 C10 1.556(4)
C14 C13 1.532(4)
C10 O3 1.477(3)
C10 C11 1.520(4)
C11 C12 1.524(5)
C12 C13 1.531(4)
C15 C20 1.393(5)
C15 C16 1.405(5)
C20 C19 1.415(6)
C16 C17 1.396(5)
C19 C18 1.397(8)
C17 C18 1.355(7)
O3 N1 1.389(3)
