#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/32/4023295.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_4023295
loop_
_publ_author_name
'John Limanto'
'C. Scott Shultz'
'Benjamin Dorner'
'Richard A. Desmond'
'Paul N. Devine'
'Shane W. Krska'
_publ_section_title
;
 Synthesis of a Tertiary Carbinamide via a Novel Rh-Catalyzed
 Asymmetric Hydrogenation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1639
_journal_page_last               1642
_journal_paper_doi               10.1021/jo702429u
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H35 Cl N2 O3'
_chemical_formula_sum            'C24 H35 Cl N2 O3'
_chemical_formula_weight         434.99
_chemical_name_common            jrc2491n
_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                   9.5172(17)
_cell_length_b                   15.659(3)
_cell_length_c                   17.026(3)
_cell_measurement_reflns_used    5824
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.55
_cell_measurement_theta_min      2.39
_cell_volume                     2537.3(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0897
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27010
_diffrn_reflns_theta_full        26.29
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.9237
_exptl_absorpt_correction_T_min  0.9174
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         5135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.890
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0533P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                3506
_reflns_number_total             5135
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702429u-File003.cif
_cod_data_source_block           jrc2491n
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023295
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3949(4) 0.7001(3) 0.21019(19) 0.1572(19) Uani 1 1 d . . .
H1A H 0.4460 0.7501 0.1943 0.236 Uiso 1 1 calc R . .
H1B H 0.3402 0.6794 0.1668 0.236 Uiso 1 1 calc R . .
H1C H 0.4597 0.6567 0.2267 0.236 Uiso 1 1 calc R . .
C2 C 0.2999(3) 0.72218(14) 0.27650(15) 0.0608(7) Uani 1 1 d . . .
C3 C 0.1894(4) 0.7825(2) 0.2476(3) 0.1391(16) Uani 1 1 d . . .
H3A H 0.1358 0.8033 0.2913 0.209 Uiso 1 1 calc R . .
H3B H 0.1283 0.7532 0.2118 0.209 Uiso 1 1 calc R . .
H3C H 0.2333 0.8296 0.2212 0.209 Uiso 1 1 calc R . .
C4 C 0.2383(4) 0.6456(2) 0.3108(2) 0.1389(18) Uani 1 1 d . . .
H4A H 0.3115 0.6103 0.3320 0.208 Uiso 1 1 calc R . .
H4B H 0.1882 0.6146 0.2710 0.208 Uiso 1 1 calc R . .
H4C H 0.1746 0.6616 0.3520 0.208 Uiso 1 1 calc R . .
C5 C 0.4901(3) 0.73918(16) 0.37211(15) 0.0596(6) Uani 1 1 d . . .
C6 C 0.6862(3) 0.78230(16) 0.45421(17) 0.0767(8) Uani 1 1 d . . .
H6A H 0.7065 0.7217 0.4506 0.092 Uiso 1 1 calc R . .
H6B H 0.6813 0.7975 0.5094 0.092 Uiso 1 1 calc R . .
C7 C 0.8026(3) 0.83271(14) 0.41482(15) 0.0606(6) Uani 1 1 d . . .
H7A H 0.8142 0.8122 0.3615 0.073 Uiso 1 1 calc R . .
H7B H 0.8900 0.8225 0.4426 0.073 Uiso 1 1 calc R . .
C8 C 0.5125(3) 0.89072(15) 0.41659(18) 0.0813(9) Uani 1 1 d . . .
H8A H 0.4992 0.9103 0.4701 0.098 Uiso 1 1 calc R . .
H8B H 0.4245 0.8980 0.3886 0.098 Uiso 1 1 calc R . .
C9 C 0.6267(2) 0.94341(14) 0.37717(15) 0.0589(6) Uani 1 1 d . . .
H9A H 0.6029 1.0034 0.3817 0.071 Uiso 1 1 calc R . .
H9B H 0.6292 0.9293 0.3217 0.071 Uiso 1 1 calc R . .
C10 C 0.7745(2) 0.92889(12) 0.41268(13) 0.0486(5) Uani 1 1 d . . .
C11 C 0.7859(3) 0.97108(12) 0.49476(12) 0.0518(6) Uani 1 1 d . . .
H11A H 0.6948 0.9723 0.5203 0.062 Uiso 1 1 calc R . .
H11B H 0.8509 0.9396 0.5277 0.062 Uiso 1 1 calc R . .
C12 C 0.8401(2) 1.06287(12) 0.48069(11) 0.0392(5) Uani 1 1 d . . .
H12 H 0.7581 1.0982 0.4682 0.047 Uiso 1 1 calc R . .
C13 C 0.8835(2) 0.97866(13) 0.36716(12) 0.0458(5) Uani 1 1 d . . .
C14 C 0.9378(3) 0.95948(14) 0.29355(14) 0.0559(6) Uani 1 1 d . . .
H14 H 0.9097 0.9105 0.2669 0.067 Uiso 1 1 calc R . .
C15 C 1.0343(3) 1.01485(17) 0.26098(13) 0.0610(7) Uani 1 1 d . . .
C16 C 0.9233(2) 1.05261(12) 0.40535(11) 0.0399(5) Uani 1 1 d . . .
C17 C 1.0219(2) 1.10625(14) 0.37152(13) 0.0507(5) Uani 1 1 d . . .
H17 H 1.0488 1.1555 0.3981 0.061 Uiso 1 1 calc R . .
C18 C 1.0818(2) 1.08837(16) 0.29870(14) 0.0585(6) Uani 1 1 d . . .
C19 C 1.1867(3) 1.1487(2) 0.26323(18) 0.0925(10) Uani 1 1 d . . .
H19A H 1.2744 1.1196 0.2556 0.139 Uiso 1 1 calc R . .
H19B H 1.2006 1.1964 0.2979 0.139 Uiso 1 1 calc R . .
H19C H 1.1523 1.1688 0.2136 0.139 Uiso 1 1 calc R . .
C20 C 0.9168(2) 1.34353(13) 0.50355(16) 0.0671(7) Uani 1 1 d . . .
H20A H 0.8936 1.3622 0.4514 0.101 Uiso 1 1 calc R . .
H20B H 1.0171 1.3407 0.5091 0.101 Uiso 1 1 calc R . .
H20C H 0.8794 1.3832 0.5411 0.101 Uiso 1 1 calc R . .
C21 C 0.8161(3) 1.10149(14) 0.62429(13) 0.0576(6) Uani 1 1 d . . .
H21A H 0.8576 1.1342 0.6660 0.086 Uiso 1 1 calc R . .
H21B H 0.8041 1.0434 0.6411 0.086 Uiso 1 1 calc R . .
H21C H 0.7263 1.1254 0.6109 0.086 Uiso 1 1 calc R . .
C22 C 0.9126(2) 1.10383(12) 0.55209(11) 0.0400(5) Uani 1 1 d . . .
C23 C 1.0517(2) 1.06030(14) 0.57073(14) 0.0567(6) Uani 1 1 d . . .
H23A H 1.1109 1.0614 0.5251 0.085 Uiso 1 1 calc R . .
H23B H 1.0346 1.0022 0.5858 0.085 Uiso 1 1 calc R . .
H23C H 1.0973 1.0899 0.6130 0.085 Uiso 1 1 calc R . .
C24 C 0.8547(2) 1.25646(13) 0.51771(12) 0.0430(5) Uani 1 1 d . . .
Cl1 Cl 1.09572(10) 0.99278(6) 0.16613(4) 0.1005(3) Uani 1 1 d . . .
N1 N 0.5521(2) 0.80004(12) 0.41686(15) 0.0776(7) Uani 1 1 d . . .
N2 N 0.94646(17) 1.19448(9) 0.53397(9) 0.0396(4) Uani 1 1 d . . .
H2 H 1.0339 1.2083 0.5340 0.048 Uiso 1 1 calc R . .
O1 O 0.3775(2) 0.77121(11) 0.33496(13) 0.0901(6) Uani 1 1 d . . .
O2 O 0.53000(19) 0.66704(11) 0.36875(11) 0.0756(5) Uani 1 1 d . . .
O3 O 0.72694(14) 1.24525(10) 0.51538(10) 0.0624(4) Uani 1 1 d . . .
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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 O1 111.3(2) . . ?
C4 C2 C1 111.0(3) . . ?
O1 C2 C1 109.4(2) . . ?
C4 C2 C3 111.6(3) . . ?
O1 C2 C3 104.4(2) . . ?
C1 C2 C3 108.9(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 O1 125.9(2) . . ?
O2 C5 N1 123.6(2) . . ?
O1 C5 N1 110.5(2) . . ?
N1 C6 C7 110.4(2) . . ?
N1 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
N1 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C10 113.3(2) . . ?
C6 C7 H7A 108.9 . . ?
C10 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C10 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N1 C8 C9 110.0(2) . . ?
N1 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 C10 113.4(2) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C13 C10 C7 113.58(19) . . ?
C13 C10 C9 110.35(18) . . ?
C7 C10 C9 108.21(17) . . ?
C13 C10 C11 101.23(16) . . ?
C7 C10 C11 112.71(18) . . ?
C9 C10 C11 110.66(18) . . ?
C12 C11 C10 106.26(17) . . ?
C12 C11 H11A 110.5 . . ?
C10 C11 H11A 110.5 . . ?
C12 C11 H11B 110.5 . . ?
C10 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C16 C12 C22 118.60(15) . . ?
C16 C12 C11 101.94(15) . . ?
C22 C12 C11 114.52(16) . . ?
C16 C12 H12 107.0 . . ?
C22 C12 H12 107.0 . . ?
C11 C12 H12 107.0 . . ?
C16 C13 C14 120.3(2) . . ?
C16 C13 C10 112.27(18) . . ?
C14 C13 C10 127.4(2) . . ?
C15 C14 C13 118.3(2) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C18 123.4(2) . . ?
C14 C15 Cl1 118.0(2) . . ?
C18 C15 Cl1 118.7(2) . . ?
C13 C16 C17 119.89(19) . . ?
C13 C16 C12 110.14(17) . . ?
C17 C16 C12 129.90(18) . . ?
C16 C17 C18 121.7(2) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C15 116.3(2) . . ?
C17 C18 C19 120.2(2) . . ?
C15 C18 C19 123.4(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C24 C20 H20A 109.5 . . ?
C24 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C24 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 C23 106.40(16) . . ?
N2 C22 C21 108.56(16) . . ?
C23 C22 C21 110.04(17) . . ?
N2 C22 C12 109.33(15) . . ?
C23 C22 C12 111.61(17) . . ?
C21 C22 C12 110.76(15) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 N2 123.39(19) . . ?
O3 C24 C20 120.85(19) . . ?
N2 C24 C20 115.75(17) . . ?
C5 N1 C6 119.6(2) . . ?
C5 N1 C8 124.5(2) . . ?
C6 N1 C8 114.3(2) . . ?
C24 N2 C22 126.52(16) . . ?
C24 N2 H2 116.7 . . ?
C22 N2 H2 116.7 . . ?
C5 O1 C2 121.97(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.487(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.457(4) . ?
C2 O1 1.458(3) . ?
C2 C3 1.496(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 O2 1.193(3) . ?
C5 O1 1.341(3) . ?
C5 N1 1.355(3) . ?
C6 N1 1.453(3) . ?
C6 C7 1.517(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C10 1.530(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.469(3) . ?
C8 C9 1.521(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.548(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C13 1.511(3) . ?
C10 C11 1.550(3) . ?
C11 C12 1.546(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C16 1.516(3) . ?
C12 C22 1.538(3) . ?
C12 H12 0.9800 . ?
C13 C16 1.381(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 C18 1.394(3) . ?
C15 Cl1 1.752(2) . ?
C16 C17 1.385(3) . ?
C17 C18 1.393(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.501(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C24 1.506(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.535(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N2 1.488(2) . ?
C22 C23 1.522(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O3 1.229(2) . ?
C24 N2 1.335(2) . ?
N2 H2 0.8600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21196731
