#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/34/2233429.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2233429
loop_
_publ_author_name
'Zeng, Tao'
'Hou, Yu-Ping'
'Ren, Wan-Zhong'
'Xu, Wen-You'
_publ_section_title
;
 Diethyl 2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate
;
_journal_coeditor_code           FB2240
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o448
_journal_paper_doi               10.1107/S1600536811054900
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C37 H56 O6'
_chemical_formula_moiety         'C37 H56 O6'
_chemical_formula_sum            'C37 H56 O6'
_chemical_formula_weight         596.82
_chemical_name_systematic
;
Diethyl 2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.344(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.006(6)
_cell_length_b                   13.610(4)
_cell_length_c                   14.252(4)
_cell_measurement_reflns_used    2211
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.30
_cell_measurement_theta_min      2.19
_cell_volume                     3614.4(18)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       'φ and ω 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  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9457
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.245
_refine_ls_extinction_coef       0.0090(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    102
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0527
_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)+(0.0716P)²+0.7136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1508
_reflns_number_gt                2010
_reflns_number_total             3280
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fb2240.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2233429
_cod_database_fobs_code          2233429
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'
'-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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.71866(9) 0.42187(11) 0.62113(12) 0.0666(5) Uani d D 1 8
H H1 0.7512(12) 0.3850(16) 0.6488(18) 0.080 Uiso d D 1 8
O O2 0.62147(8) 0.10154(10) 0.29387(12) 0.0648(5) Uani d . 1 8
O O3 0.54675(8) 0.02822(10) 0.35618(12) 0.0569(5) Uani d . 1 8
C C1 0.66141(11) 0.37176(15) 0.55316(15) 0.0447(5) Uani d . 1 8
C C2 0.64934(10) 0.27165(15) 0.56606(14) 0.0427(5) Uani d . 1 8
C C3 0.59129(11) 0.22877(15) 0.49092(14) 0.0442(5) Uani d . 1 8
H H3A 0.5820 0.1627 0.4976 0.053 Uiso calc R 1 8
C C4 0.54664(10) 0.27825(14) 0.40700(14) 0.0410(5) Uani d . 1 8
C C5 0.55917(10) 0.37794(14) 0.40102(15) 0.0442(5) Uani d . 1 8
H H5A 0.5288 0.4130 0.3460 0.053 Uiso calc R 1 8
C C6 0.61499(11) 0.42780(14) 0.47341(14) 0.0433(5) Uani d . 1 8
C C7 0.62391(12) 0.54031(16) 0.46818(17) 0.0563(6) Uani d . 1 8
C C8 0.69596(16) 0.56725(19) 0.4609(2) 0.0836(9) Uani d . 1 8
H H8A 0.6997 0.6374 0.4579 0.125 Uiso calc R 1 8
H H8B 0.6992 0.5386 0.4011 0.125 Uiso calc R 1 8
H H8C 0.7342 0.5427 0.5189 0.125 Uiso calc R 1 8
C C9 0.56543(16) 0.58469(17) 0.3764(2) 0.0934(10) Uani d . 1 8
H H9A 0.5193 0.5717 0.3801 0.140 Uiso calc R 1 8
H H9B 0.5677 0.5559 0.3162 0.140 Uiso calc R 1 8
H H9C 0.5725 0.6544 0.3753 0.140 Uiso calc R 1 8
C C10 0.61797(15) 0.58785(18) 0.5627(2) 0.0780(8) Uani d . 1 8
H H10A 0.5727 0.5708 0.5673 0.117 Uiso calc R 1 8
H H10B 0.6213 0.6580 0.5584 0.117 Uiso calc R 1 8
H H10C 0.6562 0.5645 0.6215 0.117 Uiso calc R 1 8
C C11 0.69699(12) 0.21224(15) 0.65805(15) 0.0509(6) Uani d . 1 8
C C12 0.77149(12) 0.19636(19) 0.6533(2) 0.0744(8) Uani d . 1 8
H H12A 0.7666 0.1663 0.5902 0.112 Uiso calc R 1 8
H H12B 0.7992 0.1543 0.7076 0.112 Uiso calc R 1 8
H H12C 0.7953 0.2585 0.6590 0.112 Uiso calc R 1 8
C C13 0.66642(15) 0.10925(19) 0.6605(2) 0.0815(9) Uani d . 1 8
H H13A 0.6176 0.1147 0.6563 0.122 Uiso calc R 1 8
H H13B 0.6944 0.0771 0.7223 0.122 Uiso calc R 1 8
H H13C 0.6682 0.0716 0.6046 0.122 Uiso calc R 1 8
C C14 0.7024(2) 0.2628(2) 0.75627(18) 0.1034(11) Uani d . 1 8
H H14A 0.7281 0.3236 0.7627 0.155 Uiso calc R 1 8
H H14B 0.7276 0.2208 0.8121 0.155 Uiso calc R 1 8
H H14C 0.6551 0.2757 0.7557 0.155 Uiso calc R 1 8
C C15 0.48315(10) 0.22752(14) 0.32896(15) 0.0432(5) Uani d . 1 8
H H15A 0.4486 0.2774 0.2933 0.052 Uiso calc R 1 8
H H15B 0.4604 0.1860 0.3639 0.052 Uiso calc R 1 8
C C16 0.5000 0.16358(19) 0.2500 0.0390(7) Uani d S 1 4
C C17 0.56390(11) 0.09625(14) 0.30121(16) 0.0452(5) Uani d . 1 8
C C18 0.60223(15) -0.04431(19) 0.4048(2) 0.0806(9) Uani d . 1 8
H H18A 0.6138 -0.0811 0.3544 0.097 Uiso calc R 1 8
H H18B 0.6454 -0.0117 0.4487 0.097 Uiso calc R 1 8
C C19 0.5756(2) -0.1098(2) 0.4627(3) 0.1349(15) Uani d . 1 8
H H19A 0.5583 -0.0721 0.5061 0.202 Uiso calc R 1 8
H H19B 0.6136 -0.1522 0.5027 0.202 Uiso calc R 1 8
H H19C 0.5372 -0.1487 0.4179 0.202 Uiso calc R 1 8
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 O1 H1 . . 110.7(19)
C17 O3 C18 . . 115.76(19)
O1 C1 C6 . . 115.80(19)
O1 C1 C2 . . 121.62(18)
C6 C1 C2 . . 122.53(18)
C3 C2 C1 . . 116.16(18)
C3 C2 C11 . . 121.36(18)
C1 C2 C11 . . 122.48(18)
C4 C3 C2 . . 123.98(19)
C4 C3 H3A . . 118.0
C2 C3 H3A . . 118.0
C3 C4 C5 . . 117.11(18)
C3 C4 C15 . . 121.26(18)
C5 C4 C15 . . 121.46(17)
C4 C5 C6 . . 123.08(18)
C4 C5 H5A . . 118.5
C6 C5 H5A . . 118.5
C5 C6 C1 . . 116.87(19)
C5 C6 C7 . . 121.54(17)
C1 C6 C7 . . 121.56(18)
C9 C7 C8 . . 107.1(2)
C9 C7 C10 . . 107.7(2)
C8 C7 C10 . . 109.6(2)
C9 C7 C6 . . 111.54(18)
C8 C7 C6 . . 111.67(18)
C10 C7 C6 . . 109.11(19)
C7 C8 H8A . . 109.5
C7 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C7 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C7 C9 H9A . . 109.5
C7 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C7 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
C7 C10 H10A . . 109.5
C7 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C7 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C14 C11 C12 . . 111.0(2)
C14 C11 C13 . . 106.6(2)
C12 C11 C13 . . 105.9(2)
C14 C11 C2 . . 111.06(18)
C12 C11 C2 . . 110.30(17)
C13 C11 C2 . . 111.76(18)
C11 C12 H12A . . 109.5
C11 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C11 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
C11 C13 H13A . . 109.5
C11 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C11 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
C11 C14 H14A . . 109.5
C11 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C11 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
C4 C15 C16 . . 116.22(15)
C4 C15 H15A . . 108.2
C16 C15 H15A . . 108.2
C4 C15 H15B . . 108.2
C16 C15 H15B . . 108.2
H15A C15 H15B . . 107.4
C17 C16 C17 2_655 . 106.2(2)
C17 C16 C15 2_655 2_655 110.79(10)
C17 C16 C15 . 2_655 108.55(11)
C17 C16 C15 2_655 . 108.55(11)
C17 C16 C15 . . 110.79(10)
C15 C16 C15 2_655 . 111.9(2)
O2 C17 O3 . . 123.65(19)
O2 C17 C16 . . 126.01(18)
O3 C17 C16 . . 110.34(17)
C19 C18 O3 . . 108.3(3)
C19 C18 H18A . . 110.0
O3 C18 H18A . . 110.0
C19 C18 H18B . . 110.0
O3 C18 H18B . . 110.0
H18A C18 H18B . . 108.4
C18 C19 H19A . . 109.5
C18 C19 H19B . . 109.5
H19A C19 H19B . . 109.5
C18 C19 H19C . . 109.5
H19A C19 H19C . . 109.5
H19B C19 H19C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.381(2)
O1 H1 . 0.803(16)
O2 C17 . 1.196(2)
O3 C17 . 1.336(2)
O3 C18 . 1.459(3)
C1 C6 . 1.403(3)
C1 C2 . 1.407(3)
C2 C3 . 1.389(3)
C2 C11 . 1.540(3)
C3 C4 . 1.380(3)
C3 H3A . 0.9300
C4 C5 . 1.388(3)
C4 C15 . 1.516(3)
C5 C6 . 1.390(3)
C5 H5A . 0.9300
C6 C7 . 1.547(3)
C7 C9 . 1.526(3)
C7 C8 . 1.527(4)
C7 C10 . 1.538(3)
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 0.9600
C11 C14 . 1.528(3)
C11 C12 . 1.532(3)
C11 C13 . 1.535(3)
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
C15 C16 . 1.554(2)
C15 H15A . 0.9700
C15 H15B . 0.9700
C16 C17 2_655 1.526(2)
C16 C17 . 1.526(2)
C16 C15 2_655 1.554(2)
C18 C19 . 1.442(4)
C18 H18A . 0.9700
C18 H18B . 0.9700
C19 H19A . 0.9600
C19 H19B . 0.9600
C19 H19C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O2 7_656 0.803(16) 2.38(2) 2.996(2) 134(2)
C12 H12C O2 7_656 0.96 2.46 3.398(3) 167
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O1 C1 C2 C3 . . -178.03(19)
C6 C1 C2 C3 . . 4.5(3)
O1 C1 C2 C11 . . 2.3(3)
C6 C1 C2 C11 . . -175.11(18)
C1 C2 C3 C4 . . 0.2(3)
C11 C2 C3 C4 . . 179.83(18)
C2 C3 C4 C5 . . -3.3(3)
C2 C3 C4 C15 . . -178.59(19)
C3 C4 C5 C6 . . 1.8(3)
C15 C4 C5 C6 . . 177.16(19)
C4 C5 C6 C1 . . 2.5(3)
C4 C5 C6 C7 . . -175.45(19)
O1 C1 C6 C5 . . 176.62(18)
C2 C1 C6 C5 . . -5.8(3)
O1 C1 C6 C7 . . -5.4(3)
C2 C1 C6 C7 . . 172.14(19)
C5 C6 C7 C9 . . -0.2(3)
C1 C6 C7 C9 . . -178.0(2)
C5 C6 C7 C8 . . -120.0(2)
C1 C6 C7 C8 . . 62.1(3)
C5 C6 C7 C10 . . 118.7(2)
C1 C6 C7 C10 . . -59.1(3)
C3 C2 C11 C14 . . -126.1(3)
C1 C2 C11 C14 . . 53.5(3)
C3 C2 C11 C12 . . 110.4(2)
C1 C2 C11 C12 . . -69.9(3)
C3 C2 C11 C13 . . -7.1(3)
C1 C2 C11 C13 . . 172.5(2)
C3 C4 C15 C16 . . -81.2(2)
C5 C4 C15 C16 . . 103.7(2)
C4 C15 C16 C17 . 2_655 163.70(16)
C4 C15 C16 C17 . . 47.5(2)
C4 C15 C16 C15 . 2_655 -73.76(15)
C18 O3 C17 O2 . . -2.7(3)
C18 O3 C17 C16 . . 176.81(18)
C17 C16 C17 O2 2_655 . 129.7(2)
C15 C16 C17 O2 2_655 . 10.6(3)
C15 C16 C17 O2 . . -112.6(2)
C17 C16 C17 O3 2_655 . -49.75(12)
C15 C16 C17 O3 2_655 . -168.89(16)
C15 C16 C17 O3 . . 67.9(2)
C17 O3 C18 C19 . . 178.4(3)
