#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/52/7105200.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_7105200
loop_
_publ_author_name
'Matsuo, Jun-Ichi'
'Sasaki, Shun'
'Hoshikawa, Takaya'
'Ishibashi, Hiroyuki'
_publ_section_title
;
 Intramolecular formal [4+2] cycloaddition of 3-ethoxycyclobutanones
 and alkenes.
;
_journal_issue                   6
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              934
_journal_page_last               936
_journal_paper_doi               10.1039/b919332d
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C23 H26 O2 '
_chemical_formula_sum            'C23 H26 O2'
_chemical_formula_weight         334.46
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3596(5)
_cell_length_b                   19.161(1)
_cell_length_c                   13.049(1)
_cell_measurement_reflns_used    8669
_cell_measurement_temperature    123.2
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      3.0
_cell_volume                     1840.1(2)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SHELXS86
_diffrn_ambient_temperature      123.2
_diffrn_detector_area_resol_mean 14.46
_diffrn_measured_fraction_theta_full 1.5605
_diffrn_measured_fraction_theta_max 1.5605
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21633
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             720.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.10
_refine_ls_abs_structure_Flack   0.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4049
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.0006
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00063|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0443
_reflns_number_gt                4049
_reflns_number_total             4588
_reflns_threshold_expression     F²>3.0σ(F²)
_cod_data_source_file            b919332d.txt
_cod_data_source_block           '_matsuo6'
_cod_original_sg_symbol_H-M      'P n a 21 '
_cod_original_formula_sum        'C23 H26 O2 '
_cod_database_code               7105200
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,1/2+z
1/2-x,1/2+y,1/2+z
1/2+x,1/2-y,z
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6076(1) 0.67207(5) 0.4373(3) 0.0342(3) Uani 1.00 d . . .
O2 O 0.0769(1) 0.68053(4) 0.2386(3) 0.0237(2) Uani 1.00 d . . .
C1 C 0.4450(2) 0.66051(6) 0.4326(3) 0.0225(3) Uani 1.00 d . . .
C2 C 0.3334(2) 0.68863(6) 0.3448(3) 0.0226(3) Uani 1.00 d . . .
C3 C 0.1797(2) 0.64116(6) 0.3106(3) 0.0214(3) Uani 1.00 d . . .
C4 C 0.0684(2) 0.61571(6) 0.4019(3) 0.0215(3) Uani 1.00 d . . .
C5 C 0.1921(2) 0.57554(6) 0.4761(3) 0.0202(3) Uani 1.00 d . . .
C6 C -0.0975(2) 0.57035(7) 0.7205(3) 0.0287(3) Uani 1.00 d . . .
C7 C -0.1457(2) 0.61322(8) 0.8014(3) 0.0353(4) Uani 1.00 d . . .
C8 C -0.0597(2) 0.67730(8) 0.8132(3) 0.0346(4) Uani 1.00 d . . .
C9 C 0.0724(2) 0.69773(7) 0.7440(3) 0.0291(3) Uani 1.00 d . . .
C10 C 0.1217(2) 0.65469(7) 0.6616(3) 0.0234(3) Uani 1.00 d . . .
C11 C 0.2644(2) 0.68016(6) 0.5870(3) 0.0239(3) Uani 1.00 d . . .
C12 C 0.3465(2) 0.62182(6) 0.5188(3) 0.0201(3) Uani 1.00 d . . .
C13 C 0.0862(2) 0.54115(6) 0.5635(3) 0.0233(3) Uani 1.00 d . . .
C14 C 0.0349(2) 0.59029(7) 0.6496(3) 0.0232(3) Uani 1.00 d . . .
C15 C 0.4827(2) 0.57941(6) 0.5843(3) 0.0237(3) Uani 1.00 d . . .
C16 C 0.5426(2) 0.50969(6) 0.5418(3) 0.0238(3) Uani 1.00 d . . .
C17 C 0.6213(2) 0.50242(7) 0.4447(3) 0.0289(3) Uani 1.00 d . . .
C18 C 0.6789(2) 0.43786(8) 0.4094(3) 0.0334(3) Uani 1.00 d . . .
C19 C 0.6590(2) 0.37894(7) 0.4704(3) 0.0353(3) Uani 1.00 d . . .
C20 C 0.5824(2) 0.38497(7) 0.5661(3) 0.0354(4) Uani 1.00 d . . .
C21 C 0.5249(2) 0.45003(7) 0.6014(3) 0.0288(3) Uani 1.00 d . . .
C22 C -0.0462(2) 0.63980(7) 0.1795(3) 0.0319(3) Uani 1.00 d . . .
C23 C -0.1265(2) 0.68563(8) 0.0979(3) 0.0335(4) Uani 1.00 d . . .
H1 H 0.4143 0.7024 0.2905 0.0383 Uiso 1.00 calc . . .
H2 H 0.2791 0.7317 0.3745 0.0383 Uiso 1.00 calc . . .
H3 H 0.2377 0.6033 0.2768 0.0383 Uiso 1.00 calc . . .
H4 H 0.0126 0.6490 0.4400 0.0383 Uiso 1.00 calc . . .
H5 H -0.0179 0.5811 0.3767 0.0383 Uiso 1.00 calc . . .
H6 H 0.2542 0.5412 0.4316 0.0383 Uiso 1.00 calc . . .
H7 H -0.1674 0.5239 0.7151 0.0383 Uiso 1.00 calc . . .
H8 H -0.2455 0.5953 0.8506 0.0383 Uiso 1.00 calc . . .
H9 H -0.0965 0.7130 0.8608 0.0383 Uiso 1.00 calc . . .
H10 H 0.1353 0.7433 0.7452 0.0383 Uiso 1.00 calc . . .
H11 H 0.3708 0.7018 0.6253 0.0383 Uiso 1.00 calc . . .
H12 H 0.2096 0.7134 0.5489 0.0383 Uiso 1.00 calc . . .
H13 H 0.1633 0.5067 0.5929 0.0383 Uiso 1.00 calc . . .
H14 H -0.0192 0.5176 0.5394 0.0383 Uiso 1.00 calc . . .
H15 H 0.5785 0.6101 0.5974 0.0383 Uiso 1.00 calc . . .
H16 H 0.4493 0.5688 0.6547 0.0383 Uiso 1.00 calc . . .
H17 H 0.6385 0.5420 0.3980 0.0383 Uiso 1.00 calc . . .
H18 H 0.7543 0.4327 0.3443 0.0383 Uiso 1.00 calc . . .
H19 H 0.7029 0.3321 0.4479 0.0383 Uiso 1.00 calc . . .
H20 H 0.5738 0.3419 0.6121 0.0383 Uiso 1.00 calc . . .
H21 H 0.4636 0.4525 0.6663 0.0383 Uiso 1.00 calc . . .
H22 H 0.0371 0.5998 0.1494 0.0383 Uiso 1.00 calc . . .
H23 H -0.1432 0.6190 0.2274 0.0383 Uiso 1.00 calc . . .
H24 H -0.1981 0.6619 0.0527 0.0383 Uiso 1.00 calc . . .
H25 H -0.2028 0.7263 0.1282 0.0383 Uiso 1.00 calc . . .
H26 H -0.0341 0.7079 0.0520 0.0383 Uiso 1.00 calc . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C22 113.96(10) . . . yes
O1 C1 C2 120.5(1) . . . yes
O1 C1 C12 121.1(1) . . . yes
C2 C1 C12 118.3(1) . . . yes
C1 C2 C3 114.5(1) . . . yes
O2 C3 C2 105.83(10) . . . yes
O2 C3 C4 113.54(10) . . . yes
C2 C3 C4 111.2(1) . . . yes
C3 C4 C5 109.52(10) . . . yes
C4 C5 C12 112.07(10) . . . yes
C4 C5 C13 112.6(1) . . . yes
C12 C5 C13 110.66(10) . . . yes
C7 C6 C14 121.5(1) . . . yes
C6 C7 C8 119.5(1) . . . yes
C7 C8 C9 119.9(1) . . . yes
C8 C9 C10 121.0(1) . . . yes
C9 C10 C11 118.9(1) . . . yes
C9 C10 C14 119.1(1) . . . yes
C11 C10 C14 122.0(1) . . . yes
C10 C11 C12 114.0(1) . . . yes
C1 C12 C5 111.2(1) . . . yes
C1 C12 C11 104.93(10) . . . yes
C1 C12 C15 110.7(1) . . . yes
C5 C12 C11 109.49(10) . . . yes
C5 C12 C15 111.96(10) . . . yes
C11 C12 C15 108.3(1) . . . yes
C5 C13 C14 114.3(1) . . . yes
C6 C14 C10 119.0(1) . . . yes
C6 C14 C13 119.7(1) . . . yes
C10 C14 C13 121.2(1) . . . yes
C12 C15 C16 116.8(1) . . . yes
C15 C16 C17 122.7(1) . . . yes
C15 C16 C21 119.7(1) . . . yes
C17 C16 C21 117.6(1) . . . yes
C16 C17 C18 121.0(1) . . . yes
C17 C18 C19 120.2(1) . . . yes
C18 C19 C20 119.7(1) . . . yes
C19 C20 C21 120.0(1) . . . yes
C16 C21 C20 121.5(1) . . . yes
O2 C22 C23 108.3(1) . . . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.219(2) . . yes
O2 C3 1.423(2) . . yes
O2 C22 1.423(2) . . yes
C1 C2 1.509(2) . . yes
C1 C12 1.530(2) . . yes
C2 C3 1.518(2) . . yes
C3 C4 1.526(2) . . yes
C4 C5 1.536(2) . . yes
C5 C12 1.546(2) . . yes
C5 C13 1.531(2) . . yes
C6 C7 1.383(2) . . yes
C6 C14 1.398(2) . . yes
C7 C8 1.390(2) . . yes
C8 C9 1.383(2) . . yes
C9 C10 1.403(2) . . yes
C10 C11 1.513(2) . . yes
C10 C14 1.398(2) . . yes
C11 C12 1.552(2) . . yes
C12 C15 1.547(2) . . yes
C13 C14 1.513(2) . . yes
C15 C16 1.512(2) . . yes
C16 C17 1.401(2) . . yes
C16 C21 1.389(2) . . yes
C17 C18 1.386(2) . . yes
C18 C19 1.388(2) . . yes
C19 C20 1.376(2) . . yes
C20 C21 1.395(2) . . yes
C22 C23 1.501(2) . . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C2 3.368(2) . 4_565 ?
O1 C4 3.589(2) . 1_655 ?
O2 C2 3.379(2) . 4_465 ?
O2 C20 3.595(2) . 2_664 ?
C6 C15 3.569(2) . 1_455 ?
