#------------------------------------------------------------------------------
#$Date: 2015-07-05 11:47:36 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140112 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/38/4123849.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_4123849
loop_
_publ_author_name
'Shaw, Megan H.'
'Croft, Rosemary A.'
'Whittingham, William G.'
'Bower, John F.'
_publ_section_title
;
 Modular Access to Substituted Azocanes via a Rhodium-Catalyzed
 Cycloaddition-Fragmentation Strategy.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8054
_journal_page_last               8057
_journal_paper_doi               10.1021/jacs.5b05215
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C20 H30 Cl2 N2 O8 Rh2'
_chemical_formula_sum            'C20 H30 Cl2 N2 O8 Rh2'
_chemical_formula_weight         703.18
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-04-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.336(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2575(17)
_cell_length_b                   19.844(5)
_cell_length_c                   9.142(2)
_cell_measurement_reflns_used    9817
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.88
_cell_measurement_theta_min      4.46
_cell_volume                     1299.2(5)
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Proteum CCD'
_diffrn_detector_type            'Bruker Proteum CCD'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_laue_measured_fraction_full 0.972
_diffrn_reflns_laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2291
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.258
_diffrn_reflns_theta_min         4.456
_diffrn_source                   'micro-focus rotating anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    12.573
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1353 before and 0.0737 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1678 before and 0.0782 after correction.
 The Ratio of minimum to maximum transmission is 0.23.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 23905 reflections, Rint = 0.0725
 (22594 with I > 3sig(I), Rint = 0.0725)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.442
_refine_diff_density_min         -1.397
_refine_diff_density_rms         0.182
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2291
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.351
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0580P)²+0.9613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0938
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2289
_reflns_number_total             2291
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b05215_si_005.cif
_cod_data_source_block           hklf5
_cod_depositor_comments
'Adding full bibliography for 4123848--4123850.cif.'
_cod_database_code               4123849
_shelxl_version_number           2013-3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C3 \\sim C2 \\sim O2: within 1.7A with sigma of 0.003 and sigma for terminal
atoms of 0.006
Uanis(Rh1) \\sim Ueq: with sigma of 0.0003 and sigma for terminal atoms of
0.0006
3.a Ternary CH refined with riding coordinates:
 C5(H5), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C3(H3A,H3B)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Rh1 Rh 0.62156(3) 0.58178(2) 0.49947(2) 0.01065(16) Uani 1 1 d . U
Cl1 Cl 0.32122(9) 0.54175(4) 0.56661(8) 0.0144(2) Uani 1 1 d . .
O4 O 0.5892(3) 0.59029(12) 0.0522(3) 0.0200(5) Uani 1 1 d . .
O3 O 0.4982(3) 0.59310(12) 0.2774(3) 0.0157(5) Uani 1 1 d . .
N1 N 0.8040(4) 0.60257(14) 0.2563(3) 0.0168(6) Uani 1 1 d . .
O1 O 0.8315(4) 0.56203(15) 0.8030(3) 0.0268(6) Uani 1 1 d . .
C6 C 0.6244(5) 0.59540(16) 0.1991(4) 0.0154(7) Uani 1 1 d . .
C1 C 0.7499(5) 0.57062(17) 0.6881(4) 0.0175(7) Uani 1 1 d . .
C7 C 0.3935(5) 0.58211(17) -0.0163(4) 0.0220(9) Uani 1 1 d . .
H7A H 0.3261 0.5558 0.0505 0.026 Uiso 1 1 calc R .
H7B H 0.3866 0.5570 -0.1106 0.026 Uiso 1 1 calc R .
C8 C 0.3024(5) 0.65005(18) -0.0457(4) 0.0254(8) Uani 1 1 d . .
H8A H 0.3686 0.6758 -0.1126 0.038 Uiso 1 1 calc GR .
H8B H 0.3077 0.6745 0.0480 0.038 Uiso 1 1 calc GR .
H8C H 0.1718 0.6440 -0.0917 0.038 Uiso 1 1 calc GR .
C10 C 0.9516(5) 0.6001(2) 0.1664(4) 0.0225(7) Uani 1 1 d . .
H10A H 0.9498 0.5561 0.1173 0.034 Uiso 1 1 calc GR .
H10B H 1.0727 0.6067 0.2298 0.034 Uiso 1 1 calc GR .
H10C H 0.9317 0.6358 0.0914 0.034 Uiso 1 1 calc GR .
C5 C 0.8535(4) 0.61338(16) 0.4174(3) 0.0147(6) Uani 1 1 d . .
H5 H 0.9641 0.5853 0.4588 0.018 Uiso 1 1 calc R .
O2 O 0.4934(3) 0.70275(12) 0.6224(3) 0.0244(5) Uani 1 1 d . .
C2 C 0.5887(4) 0.68077(16) 0.5382(4) 0.0183(6) Uani 1 1 d . .
C3 C 0.7037(5) 0.72286(17) 0.4485(4) 0.0202(7) Uani 1 1 d . .
H3A H 0.7215 0.7688 0.4907 0.024 Uiso 1 1 calc R .
H3B H 0.6394 0.7266 0.3447 0.024 Uiso 1 1 calc R .
C4 C 0.8927(4) 0.68797(16) 0.4537(4) 0.0181(6) Uani 1 1 d . .
H4 H 0.9579 0.7080 0.3757 0.022 Uiso 1 1 calc R .
C9 C 1.0145(5) 0.69723(18) 0.6038(4) 0.0228(7) Uani 1 1 d . .
H9A H 0.9463 0.6822 0.6820 0.034 Uiso 1 1 calc GR .
H9B H 1.0471 0.7449 0.6186 0.034 Uiso 1 1 calc GR .
H9C H 1.1288 0.6705 0.6078 0.034 Uiso 1 1 calc GR .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh 0.0927 3.6045 '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
_geom_angle_site_symmetry_3
Cl1 Rh1 Cl1 86.28(3) 3_666
O3 Rh1 Cl1 91.12(7) .
O3 Rh1 Cl1 86.24(7) 3_666
C1 Rh1 Cl1 93.51(12) .
C1 Rh1 Cl1 91.67(11) 3_666
C1 Rh1 O3 174.79(12) .
C1 Rh1 C5 93.38(14) .
C1 Rh1 C2 90.50(14) .
C5 Rh1 Cl1 91.84(9) 3_666
C5 Rh1 Cl1 172.91(9) .
C5 Rh1 O3 81.93(11) .
C2 Rh1 Cl1 175.33(11) 3_666
C2 Rh1 Cl1 97.72(10) .
C2 Rh1 O3 91.24(11) .
C2 Rh1 C5 83.90(14) .
Rh1 Cl1 Rh1 93.72(3) 3_666
C6 O4 C7 117.0(3) .
C6 O3 Rh1 108.7(2) .
C6 N1 C10 122.6(3) .
C6 N1 C5 118.2(3) .
C10 N1 C5 119.2(3) .
O4 C6 N1 114.9(3) .
O3 C6 O4 122.4(3) .
O3 C6 N1 122.7(3) .
O1 C1 Rh1 177.9(3) .
O4 C7 H7A 109.6 .
O4 C7 H7B 109.6 .
O4 C7 C8 110.1(3) .
H7A C7 H7B 108.2 .
C8 C7 H7A 109.6 .
C8 C7 H7B 109.6 .
C7 C8 H8A 109.5 .
C7 C8 H8B 109.5 .
C7 C8 H8C 109.5 .
H8A C8 H8B 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
N1 C10 H10A 109.5 .
N1 C10 H10B 109.5 .
N1 C10 H10C 109.5 .
H10A C10 H10B 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
Rh1 C5 H5 110.3 .
N1 C5 Rh1 103.87(19) .
N1 C5 H5 110.3 .
N1 C5 C4 111.3(3) .
C4 C5 Rh1 110.6(2) .
C4 C5 H5 110.3 .
O2 C2 Rh1 124.4(3) .
O2 C2 C3 125.1(3) .
C3 C2 Rh1 110.5(2) .
C2 C3 H3A 110.2 .
C2 C3 H3B 110.2 .
C2 C3 C4 107.7(3) .
H3A C3 H3B 108.5 .
C4 C3 H3A 110.2 .
C4 C3 H3B 110.2 .
C5 C4 H4 108.8 .
C3 C4 C5 107.2(2) .
C3 C4 H4 108.8 .
C9 C4 C5 111.9(3) .
C9 C4 C3 111.2(3) .
C9 C4 H4 108.8 .
C4 C9 H9A 109.5 .
C4 C9 H9B 109.5 .
C4 C9 H9C 109.5 .
H9A C9 H9B 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Rh1 Cl1 2.4885(9) .
Rh1 Cl1 2.5744(9) 3_666
Rh1 O3 2.094(2) .
Rh1 C1 1.836(4) .
Rh1 C5 2.049(3) .
Rh1 C2 2.017(3) .
Cl1 Rh1 2.5745(9) 3_666
O4 C6 1.329(4) .
O4 C7 1.465(4) .
O3 C6 1.252(4) .
N1 C6 1.331(4) .
N1 C10 1.453(5) .
N1 C5 1.474(4) .
O1 C1 1.131(5) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C7 C8 1.506(5) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C5 H5 1.0000 .
C5 C4 1.533(4) .
O2 C2 1.198(5) .
C2 C3 1.513(5) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C3 C4 1.530(5) .
C4 H4 1.0000 .
C4 C9 1.519(5) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
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
Rh1 O3 C6 O4 167.7(2)
Rh1 O3 C6 N1 -11.7(4)
Rh1 C5 C4 C3 -34.2(3)
Rh1 C5 C4 C9 87.9(3)
Rh1 C2 C3 C4 -41.1(3)
N1 C5 C4 C3 80.7(3)
N1 C5 C4 C9 -157.2(3)
C6 O4 C7 C8 87.5(4)
C6 N1 C5 Rh1 18.3(3)
C6 N1 C5 C4 -100.7(3)
C7 O4 C6 O3 0.4(5)
C7 O4 C6 N1 179.8(3)
C10 N1 C6 O4 -4.3(5)
C10 N1 C6 O3 175.2(3)
C10 N1 C5 Rh1 -161.7(3)
C10 N1 C5 C4 79.4(4)
C5 N1 C6 O4 175.8(3)
C5 N1 C6 O3 -4.8(5)
O2 C2 C3 C4 137.9(3)
C2 C3 C4 C5 48.3(3)
C2 C3 C4 C9 -74.2(3)
