#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:30:20 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178952 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/81/4118197.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_4118197
loop_
_publ_author_name
'Andrew DeAngelis'
'Olga Dmitrenko'
'Joseph M. Fox'
_publ_section_title
;
 Rh-Catalyzed Intermolecular Reactions of Cyclic α-Diazocarbonyl
 Compounds with Selectivity over Tertiary C-H Bond Migration
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11035
_journal_page_last               11043
_journal_paper_doi               10.1021/ja3046712
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C15 H17 Cl O'
_chemical_formula_weight         248.74
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.231(2)
_cell_length_b                   7.756(3)
_cell_length_c                   26.639(10)
_cell_measurement_reflns_used    943
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      3.49
_cell_volume                     1287.4(8)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       ω
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            17545
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.9525
_exptl_absorpt_correction_T_min  0.9169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.35(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0551P)²+0.1778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                3096
_reflns_number_total             3194
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3046712_si_004.cif
_cod_data_source_block           joef110
_cod_database_code               4118197
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl Cl 0.48485(7) 1.02208(6) 0.227310(14) 0.05462(13) Uani 1 1 d .
O1 O -0.1420(2) 0.59378(16) 0.50396(4) 0.0495(3) Uani 1 1 d .
C1 C -0.0151(2) 0.55220(15) 0.47156(4) 0.0319(2) Uani 1 1 d .
C2 C 0.2002(2) 0.4756(2) 0.48412(5) 0.0401(3) Uani 1 1 d .
H2A H 0.1917 0.4220 0.5178 0.048 Uiso 1 1 calc R
H2B H 0.3071 0.5698 0.4859 0.048 Uiso 1 1 calc R
C3 C 0.2800(3) 0.3406(2) 0.44687(6) 0.0432(3) Uani 1 1 d .
H3A H 0.1958 0.2333 0.4510 0.052 Uiso 1 1 calc R
H3B H 0.4323 0.3137 0.4540 0.052 Uiso 1 1 calc R
C4 C 0.2585(2) 0.40518(18) 0.39299(5) 0.0347(3) Uani 1 1 d .
H4A H 0.3077 0.3140 0.3697 0.042 Uiso 1 1 calc R
H4B H 0.3522 0.5070 0.3883 0.042 Uiso 1 1 calc R
C5 C 0.02699(19) 0.45426(14) 0.38010(4) 0.0273(2) Uani 1 1 d .
H5A H 0.0274 0.5075 0.3459 0.033 Uiso 1 1 calc R
C6 C -0.05502(19) 0.58885(15) 0.41692(4) 0.0262(2) Uani 1 1 d .
C7 C -0.0311(2) 0.78380(14) 0.40533(4) 0.0276(2) Uani 1 1 d .
H7A H -0.0072 0.8568 0.4358 0.033 Uiso 1 1 calc R
C9 C 0.2900(2) 0.91799(16) 0.36682(4) 0.0297(2) Uani 1 1 d .
H9A H 0.3455 0.9295 0.3999 0.036 Uiso 1 1 calc R
C8 C -0.2469(2) 0.69674(17) 0.40404(5) 0.0323(3) Uani 1 1 d .
H8A H -0.3491 0.7238 0.4314 0.039 Uiso 1 1 calc R
H8B H -0.3142 0.6785 0.3708 0.039 Uiso 1 1 calc R
C10 C 0.4121(2) 0.97513(16) 0.32642(5) 0.0330(2) Uani 1 1 d .
H10A H 0.5497 1.0249 0.3316 0.040 Uiso 1 1 calc R
C11 C 0.3288(2) 0.95786(17) 0.27838(5) 0.0346(3) Uani 1 1 d .
C12 C 0.1275(2) 0.8886(2) 0.27027(5) 0.0388(3) Uani 1 1 d .
H12A H 0.0716 0.8795 0.2372 0.047 Uiso 1 1 calc R
C13 C 0.0076(2) 0.83233(17) 0.31118(4) 0.0337(3) Uani 1 1 d .
H13A H -0.1311 0.7851 0.3058 0.040 Uiso 1 1 calc R
C14 C 0.0876(2) 0.84402(14) 0.35996(4) 0.0263(2) Uani 1 1 d .
C15 C -0.1222(2) 0.29766(18) 0.37853(6) 0.0399(3) Uani 1 1 d .
H15A H -0.2667 0.3346 0.3688 0.060 Uiso 1 1 calc R
H15B H -0.1274 0.2439 0.4118 0.060 Uiso 1 1 calc R
H15C H -0.0680 0.2142 0.3540 0.060 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 0.0000 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'
Cl Cl 0.1484 0.1585 '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 C6 122.01(13)
O1 C1 C2 121.82(12)
C6 C1 C2 115.94(11)
C1 C2 C3 114.62(11)
C2 C3 C4 110.99(12)
C3 C4 C5 112.05(11)
C6 C5 C15 111.01(10)
C6 C5 C4 110.03(10)
C15 C5 C4 112.40(11)
C8 C6 C1 117.32(10)
C8 C6 C5 120.24(10)
C1 C6 C5 116.03(10)
C8 C6 C7 59.13(8)
C1 C6 C7 111.17(10)
C5 C6 C7 120.58(9)
C14 C7 C8 124.38(11)
C14 C7 C6 120.95(9)
C8 C7 C6 58.74(8)
C10 C9 C14 121.56(11)
C6 C8 C7 62.13(8)
C11 C10 C9 118.57(12)
C12 C11 C10 121.44(12)
C12 C11 Cl 119.68(10)
C10 C11 Cl 118.87(11)
C11 C12 C13 119.12(12)
C12 C13 C14 121.18(13)
C13 C14 C9 118.09(11)
C13 C14 C7 123.88(12)
C9 C14 C7 118.02(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl C11 1.7449(13)
O1 C1 1.2141(17)
C1 C6 1.5039(16)
C1 C2 1.5050(19)
C2 C3 1.525(2)
C3 C4 1.526(2)
C4 C5 1.5307(18)
C5 C6 1.5208(15)
C5 C15 1.5300(18)
C6 C8 1.4993(17)
C6 C7 1.5505(17)
C7 C14 1.4918(16)
C7 C8 1.5055(18)
C9 C10 1.3905(18)
C9 C14 1.3977(18)
C10 C11 1.3877(18)
C11 C12 1.381(2)
C12 C13 1.3914(19)
C13 C14 1.3946(17)
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 C2 C3 145.57(15)
C6 C1 C2 C3 -39.78(16)
C1 C2 C3 C4 48.16(17)
C2 C3 C4 C5 -57.42(16)
C3 C4 C5 C6 56.51(14)
C3 C4 C5 C15 -67.75(15)
O1 C1 C6 C8 6.64(18)
C2 C1 C6 C8 -168.00(11)
O1 C1 C6 C5 -145.37(13)
C2 C1 C6 C5 39.99(15)
O1 C1 C6 C7 71.85(16)
C2 C1 C6 C7 -102.79(12)
C15 C5 C6 C8 -73.57(14)
C4 C5 C6 C8 161.37(11)
C15 C5 C6 C1 77.58(14)
C4 C5 C6 C1 -47.48(14)
C15 C5 C6 C7 -143.37(12)
C4 C5 C6 C7 91.58(13)
C8 C6 C7 C14 -113.97(13)
C1 C6 C7 C14 136.04(12)
C5 C6 C7 C14 -4.81(17)
C1 C6 C7 C8 -109.99(11)
C5 C6 C7 C8 109.16(12)
C1 C6 C8 C7 99.48(11)
C5 C6 C8 C7 -109.73(12)
C14 C7 C8 C6 108.28(12)
C14 C9 C10 C11 0.16(18)
C9 C10 C11 C12 1.2(2)
C9 C10 C11 Cl -177.72(10)
C10 C11 C12 C13 -1.1(2)
Cl C11 C12 C13 177.78(11)
C11 C12 C13 C14 -0.3(2)
C12 C13 C14 C9 1.56(19)
C12 C13 C14 C7 -179.06(12)
C10 C9 C14 C13 -1.49(17)
C10 C9 C14 C7 179.09(11)
C8 C7 C14 C13 2.59(18)
C6 C7 C14 C13 73.76(16)
C8 C7 C14 C9 -178.03(11)
C6 C7 C14 C9 -106.86(13)
