#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:23:00 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/88/4028862.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_4028862
loop_
_publ_author_name
'Naoki Kise'
'Yusuke Kawano'
'Toshihiko Sakurai'
_publ_section_title
;
 Reductive Coupling of Phthalimides with Ketones and Aldehydes by
 Low-Valent Titanium: One-Pot Synthesis of Alkylideneisoindolin-1-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12453
_journal_page_last               12459
_journal_paper_doi               10.1021/jo402125u
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C19 H27 N O3'
_chemical_formula_sum            'C19 H27 N O3'
_chemical_formula_weight         317.42
_chemical_melting_point          450
_chemical_name_systematic
; 
3-(4-tert-butyl-1-hydroxycyclohexyl)-3-hydroxy-2-methylisoindolin-1-one 
;
_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                 88.10(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.919(11)
_cell_length_b                   9.284(6)
_cell_length_c                   14.029(9)
_cell_measurement_temperature    298(2)
_cell_volume                     1812(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_publication_material  yadokari-XG
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12625
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0467
_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)+(0.0596P)²+0.2840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                2805
_reflns_number_total             3972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402125u_si_003.cif
_cod_data_source_block           3f
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028862
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
C1 C 0.62052(12) 0.04692(19) 1.01914(11) 0.0583(4) Uani 1 1 d .
O1 O 0.61250(10) 0.07111(16) 1.10618(8) 0.0827(5) Uani 1 1 d .
N1 N 0.59682(9) 0.13888(14) 0.94898(9) 0.0521(3) Uani 1 1 d .
C2 C 0.56077(14) 0.28359(19) 0.96777(14) 0.0731(5) Uani 1 1 d .
H1 H 0.5290 0.2863 1.0295 0.110 Uiso 1 1 calc R
H2 H 0.5160 0.3096 0.9200 0.110 Uiso 1 1 calc R
H3 H 0.6135 0.3504 0.9661 0.110 Uiso 1 1 calc R
C3 C 0.61284(10) 0.07855(15) 0.85144(9) 0.0439(3) Uani 1 1 d .
O2 O 0.52932(7) 0.09052(12) 0.79639(8) 0.0567(3) Uani 1 1 d .
H4 H 0.4864 0.0403 0.8201 0.085 Uiso 1 1 calc R
C4 C 0.69442(10) 0.16377(14) 0.79646(9) 0.0423(3) Uani 1 1 d .
O3 O 0.66153(8) 0.30854(10) 0.78520(7) 0.0550(3) Uani 1 1 d .
H5 H 0.6318 0.3149 0.7359 0.082 Uiso 1 1 calc R
C5 C 0.78694(10) 0.17339(17) 0.85429(9) 0.0481(3) Uani 1 1 d .
H6 H 0.7724 0.2213 0.9145 0.058 Uiso 1 1 calc R
H7 H 0.8093 0.0769 0.8682 0.058 Uiso 1 1 calc R
C6 C 0.86668(11) 0.25599(18) 0.79994(10) 0.0539(4) Uani 1 1 d .
H8 H 0.8471 0.3556 0.7928 0.065 Uiso 1 1 calc R
H9 H 0.9243 0.2549 0.8369 0.065 Uiso 1 1 calc R
C7 C 0.88960(11) 0.19227(15) 0.70169(10) 0.0479(3) Uani 1 1 d .
H10 H 0.9119 0.0937 0.7125 0.057 Uiso 1 1 calc R
C8 C 0.97305(12) 0.27080(18) 0.64626(11) 0.0585(4) Uani 1 1 d .
C9 C 0.99973(17) 0.1868(3) 0.55559(15) 0.0960(7) Uani 1 1 d .
H11 H 0.9451 0.1821 0.5157 0.144 Uiso 1 1 calc R
H12 H 1.0190 0.0910 0.5722 0.144 Uiso 1 1 calc R
H13 H 1.0518 0.2344 0.5219 0.144 Uiso 1 1 calc R
C10 C 0.94408(17) 0.4237(2) 0.61849(16) 0.0869(6) Uani 1 1 d .
H14 H 0.9982 0.4719 0.5887 0.130 Uiso 1 1 calc R
H15 H 0.9232 0.4757 0.6746 0.130 Uiso 1 1 calc R
H16 H 0.8926 0.4194 0.5747 0.130 Uiso 1 1 calc R
C11 C 1.06360(14) 0.2785(2) 0.70859(16) 0.0817(6) Uani 1 1 d .
H17 H 1.1163 0.3189 0.6717 0.123 Uiso 1 1 calc R
H18 H 1.0803 0.1833 0.7290 0.123 Uiso 1 1 calc R
H19 H 1.0500 0.3379 0.7634 0.123 Uiso 1 1 calc R
C12 C 0.79650(11) 0.17906(17) 0.64467(10) 0.0519(4) Uani 1 1 d .
H20 H 0.7731 0.2747 0.6303 0.062 Uiso 1 1 calc R
H21 H 0.8112 0.1306 0.5847 0.062 Uiso 1 1 calc R
C13 C 0.71777(11) 0.09572(16) 0.69931(10) 0.0482(3) Uani 1 1 d .
H22 H 0.7386 -0.0029 0.7082 0.058 Uiso 1 1 calc R
H23 H 0.6602 0.0939 0.6622 0.058 Uiso 1 1 calc R
C14 C 0.63999(11) -0.07624(15) 0.87595(11) 0.0487(3) Uani 1 1 d .
C15 C 0.64920(13) -0.19679(17) 0.81785(14) 0.0630(4) Uani 1 1 d .
H24 H 0.6366 -0.1915 0.7533 0.076 Uiso 1 1 calc R
C16 C 0.67788(15) -0.3258(2) 0.85872(19) 0.0840(6) Uani 1 1 d .
H25 H 0.6837 -0.4078 0.8209 0.101 Uiso 1 1 calc R
C17 C 0.69780(16) -0.3344(2) 0.9540(2) 0.0927(7) Uani 1 1 d .
H26 H 0.7207 -0.4204 0.9785 0.111 Uiso 1 1 calc R
C18 C 0.68433(14) -0.2172(2) 1.01394(16) 0.0832(6) Uani 1 1 d .
H27 H 0.6959 -0.2238 1.0787 0.100 Uiso 1 1 calc R
C19 C 0.65265(12) -0.08835(18) 0.97354(12) 0.0568(4) Uani 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
O1 C1 N1 125.80(18)
O1 C1 C19 126.67(16)
N1 C1 C19 107.47(14)
C1 N1 C2 122.83(15)
C1 N1 C3 113.51(13)
C2 N1 C3 123.65(14)
N1 C2 H1 109.5
N1 C2 H2 109.5
H1 C2 H2 109.5
N1 C2 H3 109.5
H1 C2 H3 109.5
H2 C2 H3 109.5
O2 C3 N1 111.71(12)
O2 C3 C14 114.12(11)
N1 C3 C14 100.23(11)
O2 C3 C4 106.60(12)
N1 C3 C4 110.29(11)
C14 C3 C4 113.91(12)
C3 O2 H4 109.5
O3 C4 C13 110.46(11)
O3 C4 C5 106.18(11)
C13 C4 C5 109.61(12)
O3 C4 C3 107.43(12)
C13 C4 C3 111.09(11)
C5 C4 C3 111.93(11)
C4 O3 H5 109.5
C6 C5 C4 111.71(12)
C6 C5 H6 109.3
C4 C5 H6 109.3
C6 C5 H7 109.3
C4 C5 H7 109.3
H6 C5 H7 107.9
C7 C6 C5 112.49(12)
C7 C6 H8 109.1
C5 C6 H8 109.1
C7 C6 H9 109.1
C5 C6 H9 109.1
H8 C6 H9 107.8
C6 C7 C12 110.11(13)
C6 C7 C8 113.59(12)
C12 C7 C8 113.69(13)
C6 C7 H10 106.3
C12 C7 H10 106.3
C8 C7 H10 106.3
C9 C8 C10 108.70(17)
C9 C8 C7 109.48(14)
C10 C8 C7 111.29(15)
C9 C8 C11 108.16(17)
C10 C8 C11 108.98(16)
C7 C8 C11 110.16(14)
C8 C9 H11 109.5
C8 C9 H12 109.5
H11 C9 H12 109.5
C8 C9 H13 109.5
H11 C9 H13 109.5
H12 C9 H13 109.5
C8 C10 H14 109.5
C8 C10 H15 109.5
H14 C10 H15 109.5
C8 C10 H16 109.5
H14 C10 H16 109.5
H15 C10 H16 109.5
C8 C11 H17 109.5
C8 C11 H18 109.5
H17 C11 H18 109.5
C8 C11 H19 109.5
H17 C11 H19 109.5
H18 C11 H19 109.5
C13 C12 C7 112.30(12)
C13 C12 H20 109.1
C7 C12 H20 109.1
C13 C12 H21 109.1
C7 C12 H21 109.1
H20 C12 H21 107.9
C12 C13 C4 111.49(12)
C12 C13 H22 109.3
C4 C13 H22 109.3
C12 C13 H23 109.3
C4 C13 H23 109.3
H22 C13 H23 108.0
C15 C14 C19 120.04(15)
C15 C14 C3 130.16(14)
C19 C14 C3 109.75(13)
C14 C15 C16 118.31(19)
C14 C15 H24 120.8
C16 C15 H24 120.8
C17 C16 C15 121.3(2)
C17 C16 H25 119.4
C15 C16 H25 119.4
C16 C17 C18 121.15(19)
C16 C17 H26 119.4
C18 C17 H26 119.4
C17 C18 C19 117.6(2)
C17 C18 H27 121.2
C19 C18 H27 121.2
C14 C19 C18 121.27(18)
C14 C19 C1 108.20(14)
C18 C19 C1 130.36(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.243(2)
C1 N1 1.352(2)
C1 C19 1.472(3)
N1 C2 1.455(2)
N1 C3 1.489(2)
C2 H1 0.9600
C2 H2 0.9600
C2 H3 0.9600
C3 O2 1.4211(19)
C3 C14 1.528(2)
C3 C4 1.566(2)
O2 H4 0.8200
C4 O3 1.4303(18)
C4 C13 1.528(2)
C4 C5 1.547(2)
O3 H5 0.8200
C5 C6 1.531(2)
C5 H6 0.9700
C5 H7 0.9700
C6 C7 1.524(2)
C6 H8 0.9700
C6 H9 0.9700
C7 C12 1.550(2)
C7 C8 1.557(2)
C7 H10 0.9800
C8 C9 1.527(3)
C8 C10 1.529(3)
C8 C11 1.559(3)
C9 H11 0.9600
C9 H12 0.9600
C9 H13 0.9600
C10 H14 0.9600
C10 H15 0.9600
C10 H16 0.9600
C11 H17 0.9600
C11 H18 0.9600
C11 H19 0.9600
C12 C13 1.527(2)
C12 H20 0.9700
C12 H21 0.9700
C13 H22 0.9700
C13 H23 0.9700
C14 C15 1.388(2)
C14 C19 1.391(2)
C15 C16 1.392(3)
C15 H24 0.9300
C16 C17 1.376(3)
C16 H25 0.9300
C17 C18 1.384(3)
C17 H26 0.9300
C18 C19 1.401(3)
C18 H27 0.9300
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
O1 C1 N1 C2 2.1(2)
C19 C1 N1 C2 179.31(14)
O1 C1 N1 C3 -178.94(14)
C19 C1 N1 C3 -1.70(16)
C1 N1 C3 O2 127.71(13)
C2 N1 C3 O2 -53.31(17)
C1 N1 C3 C14 6.46(15)
C2 N1 C3 C14 -174.56(13)
C1 N1 C3 C4 -113.93(14)
C2 N1 C3 C4 65.05(18)
O2 C3 C4 O3 57.62(13)
N1 C3 C4 O3 -63.83(14)
C14 C3 C4 O3 -175.61(11)
O2 C3 C4 C13 -63.30(15)
N1 C3 C4 C13 175.25(11)
C14 C3 C4 C13 63.47(15)
O2 C3 C4 C5 173.81(11)
N1 C3 C4 C5 52.36(16)
C14 C3 C4 C5 -59.42(15)
O3 C4 C5 C6 -63.42(15)
C13 C4 C5 C6 55.91(16)
C3 C4 C5 C6 179.64(12)
C4 C5 C6 C7 -55.58(18)
C5 C6 C7 C12 53.29(17)
C5 C6 C7 C8 -177.90(13)
C6 C7 C8 C9 172.13(16)
C12 C7 C8 C9 -60.9(2)
C6 C7 C8 C10 -67.7(2)
C12 C7 C8 C10 59.28(18)
C6 C7 C8 C11 53.31(19)
C12 C7 C8 C11 -179.73(14)
C6 C7 C12 C13 -53.81(17)
C8 C7 C12 C13 177.43(13)
C7 C12 C13 C4 56.49(17)
O3 C4 C13 C12 60.25(16)
C5 C4 C13 C12 -56.41(16)
C3 C4 C13 C12 179.37(12)
O2 C3 C14 C15 48.9(2)
N1 C3 C14 C15 168.44(16)
C4 C3 C14 C15 -73.8(2)
O2 C3 C14 C19 -128.59(14)
N1 C3 C14 C19 -9.08(15)
C4 C3 C14 C19 108.66(14)
C19 C14 C15 C16 -4.5(2)
C3 C14 C15 C16 178.20(15)
C14 C15 C16 C17 -0.7(3)
C15 C16 C17 C18 4.1(3)
C16 C17 C18 C19 -2.0(3)
C15 C14 C19 C18 6.6(2)
C3 C14 C19 C18 -175.58(14)
C15 C14 C19 C1 -169.10(14)
C3 C14 C19 C1 8.71(16)
C17 C18 C19 C14 -3.3(3)
C17 C18 C19 C1 171.36(17)
O1 C1 C19 C14 172.72(15)
N1 C1 C19 C14 -4.49(17)
O1 C1 C19 C18 -2.5(3)
N1 C1 C19 C18 -179.68(16)
