#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:18:58 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178808 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/62/4106233.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_4106233
loop_
_publ_author_name
'Vincent N. G. Lindsay'
'Cyril Nicolas'
'André B. Charette'
_publ_section_title
;
 Asymmetric Rh(II)-Catalyzed Cyclopropanation of Alkenes with Diacceptor
 Diazo Compounds: p-Methoxyphenyl Ketone as a General Stereoselectivity
 Controlling Group
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8972
_journal_page_last               8981
_journal_paper_doi               10.1021/ja201237j
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C18 H14 Cl N O2'
_chemical_formula_sum            'C18 H14 Cl N O2'
_chemical_formula_weight         311.75
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 94.675(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.940(4)
_cell_length_b                   5.2913(18)
_cell_length_c                   12.294(4)
_cell_measurement_reflns_used    3471
_cell_measurement_temperature    200
_cell_measurement_theta_max      69.03
_cell_measurement_theta_min      3.61
_cell_volume                     774.1(4)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10910
_diffrn_reflns_theta_full        72.63
_diffrn_reflns_theta_max         72.63
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    2.234
_exptl_absorpt_correction_T_max  0.9563
_exptl_absorpt_correction_T_min  0.7571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), 748 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0416
_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)+(0.0698P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                1992
_reflns_number_total             2472
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja201237j_si_004.cif
_cod_data_source_block           cha203
_cod_database_code               4106233
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
Cl24 Cl 0.96181(7) 0.0213(2) 0.09907(7) 0.0940(3) Uani 1 1 d .
C1 C 0.71718(19) 0.4749(5) 0.5554(2) 0.0494(6) Uani 1 1 d .
C2 C 0.6997(2) 0.7148(6) 0.4881(2) 0.0598(7) Uani 1 1 d .
H2A H 0.6332 0.8197 0.5005 0.072 Uiso 1 1 calc R
H2B H 0.7674 0.8123 0.4728 0.072 Uiso 1 1 calc R
C3 C 0.6798(2) 0.4748(5) 0.4298(2) 0.0519(6) Uani 1 1 d .
H3 H 0.5983 0.4355 0.4129 0.062 Uiso 1 1 calc R
C4 C 0.8337(2) 0.4175(5) 0.5857(2) 0.0574(7) Uani 1 1 d .
N4 N 0.9265(2) 0.3797(6) 0.6076(2) 0.0839(9) Uani 1 1 d .
O11 O 0.53511(14) 0.5121(5) 0.60862(15) 0.0676(5) Uani 1 1 d .
C11 C 0.6252(2) 0.4039(5) 0.6263(2) 0.0532(7) Uani 1 1 d .
C12 C 0.6398(2) 0.2097(6) 0.7131(2) 0.0510(6) Uani 1 1 d .
C13 C 0.7291(2) 0.0402(6) 0.7277(2) 0.0557(6) Uani 1 1 d .
H13 H 0.7871 0.0469 0.6793 0.067 Uiso 1 1 calc R
C14 C 0.7360(2) -0.1362(6) 0.8099(2) 0.0582(7) Uani 1 1 d .
H14 H 0.7986 -0.2474 0.8184 0.070 Uiso 1 1 calc R
C15 C 0.6514(2) -0.1519(6) 0.8806(2) 0.0555(6) Uani 1 1 d .
C16 C 0.5608(2) 0.0141(8) 0.8672(2) 0.0684(8) Uani 1 1 d .
H16 H 0.5026 0.0054 0.9153 0.082 Uiso 1 1 calc R
C17 C 0.5551(2) 0.1887(6) 0.7856(3) 0.0658(8) Uani 1 1 d .
H17 H 0.4923 0.2992 0.7775 0.079 Uiso 1 1 calc R
O18 O 0.65029(17) -0.3137(4) 0.96527(17) 0.0713(6) Uani 1 1 d .
C18 C 0.7417(3) -0.4861(8) 0.9849(3) 0.0727(8) Uani 1 1 d .
H18A H 0.8113 -0.3912 1.0027 0.109 Uiso 1 1 calc R
H18B H 0.7492 -0.5881 0.9194 0.109 Uiso 1 1 calc R
H18C H 0.7274 -0.5971 1.0460 0.109 Uiso 1 1 calc R
C21 C 0.75267(19) 0.3695(5) 0.3486(2) 0.0498(6) Uani 1 1 d .
C22 C 0.8579(2) 0.4682(6) 0.3310(2) 0.0591(7) Uani 1 1 d .
H22 H 0.8857 0.6108 0.3717 0.071 Uiso 1 1 calc R
C23 C 0.9221(2) 0.3596(6) 0.2546(2) 0.0636(8) Uani 1 1 d .
H23 H 0.9940 0.4269 0.2433 0.076 Uiso 1 1 calc R
C24 C 0.8818(2) 0.1557(6) 0.1957(2) 0.0587(7) Uani 1 1 d .
C25 C 0.7777(2) 0.0546(7) 0.2106(2) 0.0626(7) Uani 1 1 d .
H25 H 0.7504 -0.0876 0.1694 0.075 Uiso 1 1 calc R
C26 C 0.7137(2) 0.1643(6) 0.2868(2) 0.0561(7) Uani 1 1 d .
H26 H 0.6414 0.0973 0.2970 0.067 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 0.0181 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'
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'
Cl Cl 0.3639 0.7018 '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_publ_flag
C4 C1 C11 122.2(2) y
C4 C1 C2 113.7(2) y
C11 C1 C2 116.7(2) y
C4 C1 C3 116.3(2) y
C11 C1 C3 114.0(2) y
C2 C1 C3 56.64(18) y
C3 C2 C1 63.47(19) y
C3 C2 H2A 117.4 ?
C1 C2 H2A 117.4 ?
C3 C2 H2B 117.4 ?
C1 C2 H2B 117.4 ?
H2A C2 H2B 114.5 ?
C2 C3 C21 124.9(2) y
C2 C3 C1 59.90(18) y
C21 C3 C1 121.68(19) y
C2 C3 H3 113.4 ?
C21 C3 H3 113.4 ?
C1 C3 H3 113.4 ?
N4 C4 C1 177.6(3) y
O11 C11 C12 120.2(2) y
O11 C11 C1 117.0(2) y
C12 C11 C1 122.8(2) y
C13 C12 C17 116.7(3) y
C13 C12 C11 125.7(2) y
C17 C12 C11 117.6(2) y
C14 C13 C12 122.1(2) y
C14 C13 H13 118.9 ?
C12 C13 H13 118.9 ?
C13 C14 C15 119.9(3) y
C13 C14 H14 120.1 ?
C15 C14 H14 120.1 ?
O18 C15 C14 125.1(3) y
O18 C15 C16 115.8(2) y
C14 C15 C16 119.1(3) y
C17 C16 C15 120.5(2) y
C17 C16 H16 119.8 ?
C15 C16 H16 119.8 ?
C16 C17 C12 121.7(3) y
C16 C17 H17 119.1 ?
C12 C17 H17 119.1 ?
C15 O18 C18 118.7(2) y
O18 C18 H18A 109.5 ?
O18 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
O18 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C26 C21 C22 118.5(2) y
C26 C21 C3 118.3(2) y
C22 C21 C3 123.3(3) y
C23 C22 C21 120.4(3) y
C23 C22 H22 119.8 ?
C21 C22 H22 119.8 ?
C24 C23 C22 119.8(2) y
C24 C23 H23 120.1 ?
C22 C23 H23 120.1 ?
C23 C24 C25 121.2(3) y
C23 C24 CL24 119.8(2) y
C25 C24 CL24 119.0(2) y
C24 C25 C26 118.8(3) y
C24 C25 H25 120.6 ?
C26 C25 H25 120.6 ?
C21 C26 C25 121.4(2) y
C21 C26 H26 119.3 ?
C25 C26 H26 119.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl24 C24 1.736(3) y
C1 C4 1.443(3) y
C1 C11 1.504(3) y
C1 C2 1.521(4) y
C1 C3 1.573(4) y
C2 C3 1.468(4) y
C2 H2a 0.9900 ?
C2 H2b 0.9900 ?
C3 C21 1.486(3) y
C3 H3 1.0000 ?
C4 N4 1.137(3) y
O11 C11 1.222(3) y
C11 C12 1.481(4) y
C12 C13 1.394(4) y
C12 C17 1.406(3) y
C13 C14 1.373(4) y
C13 H13 0.9500 ?
C14 C15 1.387(3) y
C14 H14 0.9500 ?
C15 O18 1.349(3) y
C15 C16 1.393(4) y
C16 C17 1.361(5) y
C16 H16 0.9500 ?
C17 H17 0.9500 ?
O18 C18 1.428(4) y
C18 H18a 0.9800 ?
C18 H18b 0.9800 ?
C18 H18c 0.9800 ?
C21 C26 1.383(4) y
C21 C22 1.393(3) y
C22 C23 1.384(4) y
C22 H22 0.9500 ?
C23 C24 1.365(4) y
C23 H23 0.9500 ?
C24 C25 1.379(4) y
C25 C26 1.384(4) y
C25 H25 0.9500 ?
C26 H26 0.9500 ?
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
_geom_torsion_publ_flag
C4 C1 C2 C3 106.9(2) y
C11 C1 C2 C3 -102.3(2) y
C1 C2 C3 C21 -109.6(3) y
C4 C1 C3 C2 -102.2(3) y
C11 C1 C3 C2 107.2(3) y
C4 C1 C3 C21 12.6(4) y
C11 C1 C3 C21 -138.0(3) y
C2 C1 C3 C21 114.8(3) y
C4 C1 C11 O11 162.4(3) y
C2 C1 C11 O11 14.3(4) y
C3 C1 C11 O11 -49.0(3) y
C4 C1 C11 C12 -18.6(4) y
C2 C1 C11 C12 -166.7(2) y
C3 C1 C11 C12 130.0(2) y
O11 C11 C12 C13 167.0(3) y
C1 C11 C12 C13 -12.0(4) y
O11 C11 C12 C17 -11.3(4) y
C1 C11 C12 C17 169.7(3) y
C17 C12 C13 C14 -1.2(4) y
C11 C12 C13 C14 -179.4(3) y
C12 C13 C14 C15 1.0(5) y
C13 C14 C15 O18 -178.6(3) y
C13 C14 C15 C16 -0.5(4) y
O18 C15 C16 C17 178.6(3) y
C14 C15 C16 C17 0.2(5) y
C15 C16 C17 C12 -0.5(5) y
C13 C12 C17 C16 1.0(5) y
C11 C12 C17 C16 179.4(3) y
C14 C15 O18 C18 -0.7(4) y
C16 C15 O18 C18 -178.9(3) y
C2 C3 C21 C26 -169.2(2) y
C1 C3 C21 C26 117.5(3) y
C2 C3 C21 C22 10.3(4) y
C1 C3 C21 C22 -62.9(4) y
C26 C21 C22 C23 -1.0(4) y
C3 C21 C22 C23 179.4(3) y
C21 C22 C23 C24 0.4(5) y
C22 C23 C24 C25 0.0(5) y
C22 C23 C24 CL24 179.4(2) y
C23 C24 C25 C26 0.2(5) y
CL24 C24 C25 C26 -179.2(2) y
C22 C21 C26 C25 1.3(4) y
C3 C21 C26 C25 -179.2(3) y
C24 C25 C26 C21 -0.8(4) y
