#------------------------------------------------------------------------------
#$Date: 2017-01-19 18:11:47 +0200 (Thu, 19 Jan 2017) $
#$Revision: 190731 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/15/2001560.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2001560
loop_
_publ_author_name
'Chiaroni, A.'
'Riche, C.'
'Guingant, A.'
'd'Angelo, J.'
_publ_contact_author
;
       Dr Claude Riche
       Institut de Chimie des Substances Naturelles
      CNRS
      91198 Gif-sur-Yvette CEDEX
      France
;
_publ_section_title
;
 The asymmetric Michael process involving chiral imines: structure of
 (+-)-p-nitrobenzyl
 2-(2,2-dimethyl-1-phenylpropylamino)-1-cyclopentene-1-carboxylate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1406
_journal_page_last               1409
_journal_paper_doi               10.1107/S0108270193000320
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C24 H28 N2 O4'
_chemical_formula_sum            'C24 H28 N2 O4'
_chemical_formula_weight         408.50
_chemical_melting_point          379.0(10)
_chemical_name_systematic
;
(+-)-p-nitrobenzyl
2-(2,2-dimethyl-1-phenylpropylamino)-1-cyclopentene-1-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           'IntTabIV Table 2.2B'
_cell_angle_alpha                90.00
_cell_angle_beta                 91.74(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3630(10)
_cell_length_b                   13.536(2)
_cell_length_c                   25.703(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      21.30
_cell_measurement_theta_min      8.50
_cell_volume                     2212.8(6)
_computing_data_collection       'CAD-4  software (Enraf-Nonius, 1987)'
_computing_data_reduction        'NONIUS (Riche, 1989)'
_computing_molecular_graphics    'R3M  (Riche, 1983); ORTEP (Johnson, 1965)'
_computing_publication_material  'ACTACIF (Riche, 1992)'
_computing_structure_refinement  'SHELX76   (Sheldrick, 1976)'
_computing_structure_solution    'SHELXS86  (Sheldrick, 1986)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Nonius CAD4 diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3853
_diffrn_reflns_theta_max         64.93
_diffrn_reflns_theta_min         3.26
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  180
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.64
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.23
_exptl_crystal_description       prism
_exptl_crystal_F_000             872.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.44
_refine_ls_hydrogen_treatment    'noref; U~iso~(H) = 1.10U~eq~(bonded atom)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2239
_refine_ls_R_factor_obs          0.072
_refine_ls_shift/esd_max         0.05
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F)+0.0045F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.113
_reflns_number_observed          2272
_reflns_number_total             3764
_reflns_observed_criterion       I>3.0\s(I)
_cod_data_source_file            pa1038.cif
_cod_data_source_block           terbutyl
_cod_depositor_comments
;
 Adding the _atom_site_type_symbol data item.

 Antanas Vaitkus,
 2017-01-19

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(F)+0.0045F^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(F)+0.0045F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2212.8(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2001560
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,-y,-z
-x,1/2+y,1/2-z
+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
C1 C 0.4983(7) 0.5317(3) 0.1043(2) 0.047(4) Uani ? ?
C2 C 0.6439(7) 0.5962(3) 0.0870(2) 0.044(4) Uani ? ?
C3 C 0.7964(8) 0.5446(3) 0.0520(2) 0.056(5) Uani ? ?
C4 C 0.7206(9) 0.4385(4) 0.0494(2) 0.073(6) Uani ? ?
C5 C 0.5305(8) 0.4288(3) 0.0838(2) 0.055(5) Uani ? ?
C6 C 0.3404(7) 0.5627(3) 0.1386(2) 0.049(4) Uani ? ?
C7 C 0.8119(6) 0.7614(3) 0.0780(2) 0.046(4) Uani ? ?
C8 C 0.7574(7) 0.7867(3) 0.0213(2) 0.045(4) Uani ? ?
C9 C 0.9129(8) 0.7904(4) -0.0150(2) 0.058(5) Uani ? ?
C10 C 0.8673(11) 0.8168(4) -0.0653(2) 0.080(7) Uani ? ?
C11 C 0.6671(13) 0.8386(4) -0.0818(2) 0.083(8) Uani ? ?
C12 C 0.5110(11) 0.8329(5) -0.0469(3) 0.089(8) Uani ? ?
C13 C 0.5519(8) 0.8055(4) 0.0047(2) 0.064(6) Uani ? ?
C14 C 0.8341(8) 0.8525(4) 0.1138(2) 0.055(5) Uani ? ?
C15 C 0.6253(10) 0.9075(4) 0.1191(3) 0.078(7) Uani ? ?
C16 C 0.9126(10) 0.8186(4) 0.1673(2) 0.078(7) Uani ? ?
C17 C 0.9910(11) 0.9244(5) 0.0917(3) 0.093(8) Uani ? ?
C18 C 0.0468(7) 0.5131(3) 0.1871(2) 0.057(5) Uani ? ?
C19 C -0.0797(7) 0.4211(3) 0.1978(2) 0.045(4) Uani ? ?
C20 C -0.0101(7) 0.3281(3) 0.1852(2) 0.052(5) Uani ? ?
C21 C -0.1295(7) 0.2462(3) 0.1956(2) 0.056(5) Uani ? ?
C22 C -0.3219(6) 0.2594(3) 0.2174(2) 0.045(4) Uani ? ?
C23 C -0.3983(7) 0.3527(3) 0.2303(2) 0.052(5) Uani ? ?
C24 C -0.2729(7) 0.4325(3) 0.2206(2) 0.050(5) Uani ? ?
N1 N 0.6621(6) 0.6927(3) 0.0990(2) 0.050(4) Uani ? ?
N2 N -0.4564(7) 0.1731(3) 0.2252(2) 0.056(4) Uani ? ?
O1 O 0.3169(6) 0.6459(2) 0.1557(2) 0.069(4) Uani ? ?
O2 O 0.2102(5) 0.4881(2) 0.15200(10) 0.056(3) Uani ? ?
O3 O -0.3846(6) 0.0914(3) 0.2154(2) 0.075(4) Uani ? ?
O4 O -0.6369(6) 0.1855(3) 0.2404(2) 0.088(5) Uani ? ?
H31 H 0.79324 0.57513 0.01657 0.062 Uiso calc C3
H32 H 0.94259 0.54797 0.06736 0.062 Uiso calc C3
H41 H 0.67965 0.42104 0.01266 0.080 Uiso calc C4
H42 H 0.83479 0.39305 0.06226 0.080 Uiso calc C4
H51 H 0.55997 0.38142 0.11296 0.060 Uiso calc C5
H52 H 0.40433 0.40601 0.06294 0.060 Uiso calc C5
H7 H 0.95294 0.72887 0.07723 0.052 Uiso calc C7
H9 H 1.06094 0.77334 -0.00439 0.065 Uiso calc C9
H10 H 0.98295 0.82017 -0.09076 0.087 Uiso calc C10
H11 H 0.63576 0.85895 -0.11858 0.092 Uiso calc C11
H12 H 0.36332 0.84798 -0.05870 0.098 Uiso calc C12
H13 H 0.43420 0.79967 0.02939 0.070 Uiso calc C13
H151 H 0.51875 0.86172 0.13373 0.087 Uiso calc C15
H152 H 0.57453 0.93122 0.08409 0.087 Uiso calc C15
H153 H 0.64619 0.96527 0.14294 0.087 Uiso calc C15
H161 H 0.80876 0.77144 0.18192 0.088 Uiso calc C16
H162 H 0.92850 0.87707 0.19082 0.088 Uiso calc C16
H163 H 1.05155 0.78487 0.16433 0.088 Uiso calc C16
H171 H 1.12900 0.89023 0.08785 0.105 Uiso calc C17
H172 H 1.00974 0.98211 0.11566 0.105 Uiso calc C17
H173 H 0.93807 0.94807 0.05680 0.105 Uiso calc C17
H181 H 0.11061 0.53911 0.22038 0.064 Uiso calc C18
H182 H -0.04682 0.56463 0.17084 0.064 Uiso calc C18
H20 H 0.12854 0.31990 0.16845 0.058 Uiso calc C20
H21 H -0.07770 0.17834 0.18737 0.062 Uiso calc C21
H23 H -0.53912 0.36086 0.24601 0.058 Uiso calc C23
H24 H -0.32196 0.50017 0.22998 0.055 Uiso calc C24
HN1 H 0.57600 0.71750 0.12650 0.055 Uiso calc N1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 1 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C5 . . . 112.3(4) yes
C2 C1 C6 . . . 121.0(4) yes
C5 C1 C6 . . . 126.7(4) yes
C1 C2 C3 . . . 110.7(4) yes
C1 C2 N1 . . . 127.1(4) yes
C3 C2 N1 . . . 122.2(4) yes
C2 C3 C4 . . . 104.8(4) yes
C3 C4 C5 . . . 108.2(4) yes
C1 C5 C4 . . . 104.0(4) yes
C1 C6 O1 . . . 126.4(4) yes
C1 C6 O2 . . . 112.7(4) yes
O1 C6 O2 . . . 120.9(4) yes
C8 C7 C14 . . . 113.9(4) yes
C8 C7 N1 . . . 111.6(3) yes
C14 C7 N1 . . . 109.8(3) yes
C7 C8 C9 . . . 120.4(4) yes
C7 C8 C13 . . . 121.3(4) yes
C9 C8 C13 . . . 118.2(4) yes
C8 C9 C10 . . . 120.9(5) yes
C9 C10 C11 . . . 121.4(6) yes
C10 C11 C12 . . . 118.6(6) yes
C11 C12 C13 . . . 121.6(6) yes
C8 C13 C12 . . . 119.3(5) yes
C7 C14 C15 . . . 112.2(4) yes
C7 C14 C16 . . . 108.7(4) yes
C7 C14 C17 . . . 109.7(4) yes
C15 C14 C16 . . . 109.2(4) yes
C15 C14 C17 . . . 107.7(5) yes
C16 C14 C17 . . . 109.3(5) yes
C19 C18 O2 . . . 108.6(4) yes
C18 C19 C20 . . . 122.3(4) yes
C18 C19 C24 . . . 117.9(4) yes
C20 C19 C24 . . . 119.8(4) yes
C19 C20 C21 . . . 120.6(4) yes
C20 C21 C22 . . . 118.6(4) yes
C21 C22 C23 . . . 122.4(4) yes
C21 C22 N2 . . . 118.9(4) yes
C23 C22 N2 . . . 118.6(4) yes
C22 C23 C24 . . . 117.4(4) yes
C19 C24 C23 . . . 121.2(4) yes
C2 N1 C7 . . . 126.1(4) yes
C22 N2 O3 . . . 117.9(4) yes
C22 N2 O4 . . . 119.2(4) yes
O3 N2 O4 . . . 122.9(4) yes
C6 O2 C18 . . . 116.2(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . . 1.358(6) yes
C1 C5 . . 1.506(6) yes
C1 C6 . . 1.421(6) yes
C2 C3 . . 1.514(6) yes
C2 N1 . . 1.346(6) yes
C3 C4 . . 1.516(7) yes
C4 C5 . . 1.525(8) yes
C6 O1 . . 1.219(6) yes
C6 O2 . . 1.357(5) yes
C7 C8 . . 1.526(6) yes
C7 C14 . . 1.543(6) yes
C7 N1 . . 1.448(5) yes
C8 C9 . . 1.382(7) yes
C8 C13 . . 1.387(7) yes
C9 C10 . . 1.364(8) yes
C10 C11 . . 1.362(11) yes
C11 C12 . . 1.360(10) yes
C12 C13 . . 1.393(9) yes
C14 C15 . . 1.532(8) yes
C14 C16 . . 1.519(8) yes
C14 C17 . . 1.518(8) yes
C18 C19 . . 1.513(6) yes
C18 O2 . . 1.438(6) yes
C19 C20 . . 1.376(6) yes
C19 C24 . . 1.387(6) yes
C20 C21 . . 1.375(6) yes
C21 C22 . . 1.374(6) yes
C22 C23 . . 1.397(6) yes
C22 N2 . . 1.465(6) yes
C23 C24 . . 1.370(6) yes
N2 O3 . . 1.227(5) yes
N2 O4 . . 1.236(6) yes
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
C2 N1 C7 C8 71.8(4) yes
C2 N1 C7 C14 -161.0(5) yes
N1 C7 C8 C13 42.8(4) yes
N1 C7 C14 C16 60.5(4) yes
N1 C7 C14 C15 -60.3(4) yes
N1 C7 C14 C17 -180.0(5) yes
C1 C2 N1 C7 -176.6(5) yes
C1 C2 C3 C4 1.1(4) yes
C2 C3 C4 C5 -1.6(4) yes
C3 C4 C5 C1 1.5(4) yes
C4 C5 C1 C2 -0.9(4) yes
C5 C1 C2 C3 -0.2(3) yes
N1 C2 C1 C6 0.7(4) yes
C2 C1 C6 O1 0.1(4) yes
C2 C1 C6 O2 -179.6(5) yes
C1 C6 O2 C18 179.4(5) yes
C6 O2 C18 C19 -179.4(5) yes
O2 C18 C19 C20 14.2(3) yes
C21 C22 N2 O3 5.4(4) yes
