#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/41/1504127.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_1504127
loop_
_publ_author_name
'Marqués-López, Eugenia'
'Herrera, Raquel P.'
'Marks, Timo'
'Jacobs, Wiebke C.'
'Könning, Daniel'
'de Figueiredo, Renata M.'
'Christmann, Mathias'
_publ_section_title
;
 Crossed intramolecular Rauhut-Currier-type reactions via dienamine
 activation.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4116
_journal_page_last               4119
_journal_paper_doi               10.1021/ol901614t
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H15 Cl O2'
_chemical_formula_sum            'C15 H15 Cl O2'
_chemical_formula_weight         262.72
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-04-15T16:46:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2032(2)
_cell_length_b                   12.4052(4)
_cell_length_c                   20.7454(7)
_cell_measurement_reflns_used    12422
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.1491
_cell_measurement_theta_min      2.5578
_cell_volume                     1339.05(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.953
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29382
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1359 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0324P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0599
_reflns_number_gt                2539
_reflns_number_total             3365
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901614t_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1504127
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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 0.95828(7) -0.65915(3) -0.983807(17) 0.04211(11) Uani 1 1 d .
O1 O 0.1157(2) -0.38792(7) -0.80487(5) 0.0469(3) Uani 1 1 d .
O2 O -0.2786(2) -0.11014(9) -0.93686(5) 0.0508(3) Uani 1 1 d .
C1 C 0.7488(3) -0.56909(10) -0.94631(6) 0.0302(3) Uani 1 1 d .
C2 C 0.5656(3) -0.60866(9) -0.90486(6) 0.0362(3) Uani 1 1 d .
H2 H 0.5522 -0.6839 -0.8972 0.043 Uiso 1 1 calc R
C3 C 0.4024(3) -0.53786(10) -0.87477(6) 0.0360(3) Uani 1 1 d .
H3 H 0.2763 -0.5647 -0.8458 0.043 Uiso 1 1 calc R
C4 C 0.4184(3) -0.42736(9) -0.88600(6) 0.0275(3) Uani 1 1 d .
C5 C 0.6033(3) -0.39028(10) -0.92856(6) 0.0317(3) Uani 1 1 d .
H5 H 0.6152 -0.3152 -0.9372 0.038 Uiso 1 1 calc R
C6 C 0.7706(3) -0.46029(10) -0.95873(6) 0.0330(3) Uani 1 1 d .
H6 H 0.8982 -0.4341 -0.9875 0.04 Uiso 1 1 calc R
C7 C 0.2387(3) -0.35420(10) -0.85032(6) 0.0310(3) Uani 1 1 d .
C8 C 0.2143(3) -0.23900(9) -0.87310(6) 0.0318(3) Uani 1 1 d .
H81 H 0.1339 -0.2388 -0.9164 0.038 Uiso 1 1 calc R
H82 H 0.3885 -0.2078 -0.8774 0.038 Uiso 1 1 calc R
C9 C 0.0558(3) -0.16740(9) -0.82827(6) 0.0315(3) Uani 1 1 d .
H9 H -0.1142 -0.2017 -0.819 0.038 Uiso 1 1 calc R
C10 C 0.0178(3) -0.05667(10) -0.85736(6) 0.0326(3) Uani 1 1 d .
C11 C 0.1629(3) 0.01846(10) -0.82850(7) 0.0382(3) Uani 1 1 d .
C12 C 0.3150(3) -0.02901(11) -0.77489(6) 0.0449(4) Uani 1 1 d .
H121 H 0.2999 0.0153 -0.7354 0.054 Uiso 1 1 calc R
H122 H 0.4987 -0.035 -0.7868 0.054 Uiso 1 1 calc R
C13 C 0.1962(3) -0.14051(10) -0.76482(6) 0.0436(4) Uani 1 1 d .
H131 H 0.0738 -0.1394 -0.7283 0.052 Uiso 1 1 calc R
H132 H 0.3314 -0.1946 -0.7558 0.052 Uiso 1 1 calc R
C14 C -0.1509(3) -0.03956(12) -0.91185(7) 0.0412(4) Uani 1 1 d .
H14 H -0.1626 0.0312 -0.9291 0.049 Uiso 1 1 calc R
C15 C 0.1879(4) 0.13621(11) -0.84362(8) 0.0595(5) Uani 1 1 d .
H151 H 0.0854 0.1533 -0.8819 0.089 Uiso 1 1 calc R
H152 H 0.3687 0.1535 -0.8519 0.089 Uiso 1 1 calc R
H153 H 0.1261 0.1787 -0.807 0.089 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'
H H 0 0 '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'
O O 0.0106 0.006 '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
C2 C1 C6 121.57(12)
C2 C1 Cl1 118.93(10)
C6 C1 Cl1 119.51(11)
C3 C2 C1 119.04(11)
C2 C3 C4 121.12(13)
C5 C4 C3 118.37(13)
C5 C4 C7 123.19(11)
C3 C4 C7 118.42(12)
C6 C5 C4 121.24(12)
C1 C6 C5 118.66(13)
O1 C7 C4 120.26(11)
O1 C7 C8 121.65(12)
C4 C7 C8 118.08(11)
C7 C8 C9 113.88(10)
C10 C9 C8 110.82(10)
C10 C9 C13 101.88(10)
C8 C9 C13 112.93(12)
C11 C10 C14 126.05(12)
C11 C10 C9 112.32(12)
C14 C10 C9 121.59(12)
C10 C11 C12 111.00(12)
C10 C11 C15 129.26(15)
C12 C11 C15 119.73(14)
C11 C12 C13 104.19(12)
C12 C13 C9 105.70(10)
O2 C14 C10 124.02(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7438(13)
O1 C7 1.2138(15)
O2 C14 1.2153(18)
C1 C2 1.3746(19)
C1 C6 1.3786(17)
C2 C3 1.3720(19)
C3 C4 1.3930(17)
C4 C5 1.3845(18)
C4 C7 1.4987(18)
C5 C6 1.3798(19)
C7 C8 1.5105(17)
C8 C9 1.5277(17)
C9 C10 1.5132(17)
C9 C13 1.5421(18)
C10 C11 1.340(2)
C10 C14 1.447(2)
C11 C12 1.487(2)
C11 C15 1.4996(18)
C12 C13 1.529(2)
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
C6 C1 C2 C3 -0.6(2)
Cl1 C1 C2 C3 179.31(11)
C1 C2 C3 C4 0.5(2)
C2 C3 C4 C5 0.2(2)
C2 C3 C4 C7 -178.49(12)
C3 C4 C5 C6 -0.8(2)
C7 C4 C5 C6 177.78(12)
C2 C1 C6 C5 0.0(2)
Cl1 C1 C6 C5 -179.94(10)
C4 C5 C6 C1 0.7(2)
C5 C4 C7 O1 -165.66(13)
C3 C4 C7 O1 12.92(19)
C5 C4 C7 C8 15.00(19)
C3 C4 C7 C8 -166.43(13)
O1 C7 C8 C9 8.61(19)
C4 C7 C8 C9 -172.05(12)
C7 C8 C9 C10 -174.41(12)
C7 C8 C9 C13 72.02(15)
C8 C9 C10 C11 -105.92(13)
C13 C9 C10 C11 14.47(15)
C8 C9 C10 C14 71.78(17)
C13 C9 C10 C14 -167.83(12)
C14 C10 C11 C12 -178.97(13)
C9 C10 C11 C12 -1.39(16)
C14 C10 C11 C15 0.6(3)
C9 C10 C11 C15 178.14(14)
C10 C11 C12 C13 -12.56(16)
C15 C11 C12 C13 167.86(13)
C11 C12 C13 C9 20.96(15)
C10 C9 C13 C12 -21.19(15)
C8 C9 C13 C12 97.71(13)
C11 C10 C14 O2 179.63(14)
C9 C10 C14 O2 2.3(2)
