#------------------------------------------------------------------------------
#$Date: 2017-02-04 15:13:57 +0100 (Sat 04 de Feb de 2017) $
#$Revision: 191739 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/54/7155407.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_7155407
loop_
_publ_author_name
'Pereira, Raul'
'Pfeifer, Lukas'
'Fournier, Jean'
'Gouverneur, Véronique'
'Cvengroš, Ján'
_publ_section_title
;
 Twisting the ethano-Tröger's base: the bisamide.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              628
_journal_page_last               633
_journal_paper_doi               10.1039/c6ob02359b
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.34
_chemical_melting_point          593
_space_group_IT_number           30
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 -2bc'
_symmetry_space_group_name_H-M   'P n c 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2015-12-11
_audit_creation_method           CRYSTALS_ver_14.43
_audit_update_record
;
2015-12-11 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3791(1)
_cell_length_b                   12.5501(2)
_cell_length_c                   7.4981(1)
_cell_measurement_reflns_used    10384
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     694.387(17)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13587
_diffrn_reflns_theta_full        76.363
_diffrn_reflns_theta_max         76.363
_diffrn_reflns_theta_min         5.997
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.13
_refine_ls_abs_structure_details 'Flack (1983), 669 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1455
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.0001704
_refine_ls_shift/su_mean         0.0000200
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.11P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0692
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0692
_reflns_limit_h_max              9
_reflns_limit_h_min              0
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              -9
_reflns_number_gt                1451
_reflns_number_total             1461
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   1.84
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0253
_oxford_refine_ls_scale          11.9(6)
_oxford_reflns_number_all        1455
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 034lp14
_cod_data_source_file            c6ob02359b2.cif
_cod_data_source_block           4a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '593 K' was changed to '593' - the
value should be numeric and without a unit designator.

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155403--7155407.cif.
;
_cod_original_sg_symbol_H-M      'P n c 2 '
_cod_database_code               7155407
_iucr_refine_instructions_details_constraints
;
#
# Punched on 11/12/15 at 11:24:41
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 103,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 112,X'S) H   ( 111,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
#
# Punched on 11/12/15 at 11:24:41
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z
-x,y+1/2,z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
O1 O 0.28594(10) 0.43730(6) 0.33692(17) 0.0251 1.0000 Uani .
C2 C 0.31960(12) 0.47647(8) 0.19247(19) 0.0194 1.0000 Uani .
N3 N 0.39003(12) 0.41564(6) 0.05205(17) 0.0193 1.0000 Uani .
C4 C 0.54757(14) 0.35156(8) 0.09517(19) 0.0194 1.0000 Uani .
C5 C 0.70058(13) 0.40585(8) 0.15791(19) 0.0198 1.0000 Uani .
C6 C 0.85875(14) 0.34967(9) 0.19589(19) 0.0217 1.0000 Uani .
C7 C 0.86791(13) 0.24033(9) 0.16412(19) 0.0234 1.0000 Uani .
C8 C 0.71590(15) 0.18884(8) 0.09524(19) 0.0232 1.0000 Uani .
C9 C 0.55447(14) 0.24312(9) 0.06158(19) 0.0215 1.0000 Uani .
C10 C 1.04012(15) 0.17982(10) 0.2031(2) 0.0314 1.0000 Uani .
C11 C 0.41240(13) 0.46668(8) -0.12304(19) 0.0211 1.0000 Uani .
H61 H 0.9618 0.3856 0.2468 0.0266 1.0000 Uiso R
H81 H 0.7226 0.1135 0.0683 0.0272 1.0000 Uiso R
H91 H 0.4526 0.2081 0.0110 0.0273 1.0000 Uiso R
H101 H 1.0789 0.1366 0.1045 0.0504 1.0000 Uiso R
H103 H 1.1383 0.2276 0.2350 0.0499 1.0000 Uiso R
H102 H 1.0223 0.1310 0.2997 0.0509 1.0000 Uiso R
H112 H 0.3066 0.5111 -0.1444 0.0235 1.0000 Uiso R
H111 H 0.4192 0.4124 -0.2128 0.0221 1.0000 Uiso R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0226(4) 0.0265(4) 0.0262(4) 0.0049(3) 0.0052(3) 0.0001(3)
C2 0.0125(4) 0.0222(5) 0.0236(5) 0.0012(4) -0.0013(4) -0.0019(3)
N3 0.0164(4) 0.0194(4) 0.0219(5) 0.0002(3) -0.0004(3) -0.0006(3)
C4 0.0182(4) 0.0206(4) 0.0195(4) 0.0010(4) 0.0017(4) 0.0007(4)
C5 0.0180(4) 0.0210(5) 0.0203(5) 0.0001(4) 0.0023(4) 0.0002(3)
C6 0.0179(4) 0.0260(5) 0.0213(5) 0.0011(4) 0.0020(4) 0.0009(4)
C7 0.0227(5) 0.0278(5) 0.0197(5) 0.0039(4) 0.0053(4) 0.0060(4)
C8 0.0294(5) 0.0189(5) 0.0213(5) 0.0013(4) 0.0064(4) 0.0027(4)
C9 0.0236(5) 0.0215(5) 0.0194(5) 0.0009(4) 0.0023(4) -0.0024(4)
C10 0.0270(6) 0.0325(6) 0.0347(6) 0.0016(5) 0.0024(5) 0.0118(4)
C11 0.0202(4) 0.0236(5) 0.0196(5) -0.0002(4) -0.0017(4) -0.0004(4)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C5 2_665 C2 O1 121.98(9) yes
C5 2_665 C2 N3 116.21(9) yes
O1 . C2 N3 121.70(9) yes
C2 . N3 C4 115.60(8) yes
C2 . N3 C11 118.39(8) yes
C4 . N3 C11 110.54(8) yes
N3 . C4 C5 116.84(8) yes
N3 . C4 C9 122.27(9) yes
C5 . C4 C9 120.64(9) yes
C2 2_665 C5 C4 117.07(8) yes
C2 2_665 C5 C6 122.94(9) yes
C4 . C5 C6 119.87(9) yes
C5 . C6 C7 120.25(10) yes
C5 . C6 H61 120.4 no
C7 . C6 H61 119.4 no
C6 . C7 C8 118.72(9) yes
C6 . C7 C10 120.20(10) yes
C8 . C7 C10 121.08(10) yes
C7 . C8 C9 121.86(9) yes
C7 . C8 H81 119.3 no
C9 . C8 H81 118.9 no
C8 . C9 C4 118.57(10) yes
C8 . C9 H91 121.5 no
C4 . C9 H91 119.9 no
C7 . C10 H101 112.7 no
C7 . C10 H103 111.5 no
H101 . C10 H103 108.4 no
C7 . C10 H102 110.6 no
H101 . C10 H102 105.1 no
H103 . C10 H102 108.2 no
C11 2_665 C11 N3 109.33(6) yes
C11 2_665 C11 H112 111.2 no
N3 . C11 H112 107.9 no
C11 2_665 C11 H111 110.0 no
N3 . C11 H111 108.9 no
H112 . C11 H111 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.2151(13) yes
C2 C5 2_665 1.5068(13) yes
C2 N3 . 1.4006(13) yes
N3 C4 . 1.4501(12) yes
N3 C11 . 1.4701(13) yes
C4 C5 . 1.4002(14) yes
C4 C9 . 1.3849(14) yes
C5 C6 . 1.3930(13) yes
C6 C7 . 1.3944(16) yes
C6 H61 . 0.963 no
C7 C8 . 1.3937(15) yes
C7 C10 . 1.5089(14) yes
C8 C9 . 1.3952(15) yes
C8 H81 . 0.968 no
C9 H91 . 0.949 no
C10 H101 . 0.961 no
C10 H103 . 0.970 no
C10 H102 . 0.958 no
C11 C11 2_665 1.5397(19) yes
C11 H112 . 0.973 no
C11 H111 . 0.959 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 H61 O1 1_655 163.32 0.963 2.569 3.5021(16) yes
C9 H91 O1 4_554 156.06 0.949 2.559 3.4483(16) yes
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
0 0 2 x
