#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/76/4027629.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_4027629
loop_
_publ_author_name
'Diego Núñez-Villanueva'
'Lourdes Infantes'
'M. Teresa García-López'
'Rosario González-Muñiz'
'Mercedes Martín-Martínez'
_publ_contact_author_address
;Department of Crystallography
Instituto de Quimica-Fisica Rocasolano
Serrano 119
28006-Madrid, Spain
;
_publ_contact_author_email       xlourdes@iqfr.csic.es
_publ_contact_author_fax         00(34)915619400
_publ_contact_author_name        'Infantes, L.'
_publ_contact_author_phone       00(34)915642431
_publ_section_title
;
 Azepane Quaternary Amino Acids As Effective Inducers of 310Helix
 Conformations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9833
_journal_page_last               9839
_journal_paper_doi               10.1021/jo301379r
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C23 H39 N5 O6 , C4 H8 O2'
_chemical_formula_sum            'C27 H47 N5 O8'
_chemical_formula_weight         569.7
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-05-09
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6864(5)
_cell_length_b                   17.6725(12)
_cell_length_c                   20.2622(13)
_cell_measurement_reflns_used    2329
_cell_measurement_temperature    120(2)
_cell_volume                     3110.5(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 14
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       '135mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD2000
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0068092
_diffrn_orient_matrix_UB_12      -0.0564106
_diffrn_orient_matrix_UB_13      -0.0025456
_diffrn_orient_matrix_UB_21      -0.0756638
_diffrn_orient_matrix_UB_22      0
_diffrn_orient_matrix_UB_23      -0.0371962
_diffrn_orient_matrix_UB_31      0.0864975
_diffrn_orient_matrix_UB_32      0.0044407
_diffrn_orient_matrix_UB_33      -0.032337
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            4179
_diffrn_reflns_theta_full        57.89
_diffrn_reflns_theta_max         57.89
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.74
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       prism
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.07
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         4179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1050P)²+0.8162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                4024
_reflns_number_total             4179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301379r_si_002.cif
_cod_data_source_block           dn267
_cod_original_sg_symbol_Hall     P2ac2ab
_cod_database_code               4027629
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
H4 H 0.386(3) 0.4741(15) 0.5775(15) 0.000(7) Uiso 1 1 d .
H2 H 0.236(3) 0.4833(15) 0.3632(17) 0.019(8) Uiso 1 1 d .
H5 H 0.115(3) 0.4414(15) 0.6279(16) 0.017(7) Uiso 1 1 d .
H3 H 0.394(3) 0.3908(14) 0.4538(16) 0.010(7) Uiso 1 1 d .
C1 C -0.0510(3) 0.41370(16) 0.33208(14) 0.0254(6) Uani 1 1 d .
H1A H -0.0019 0.4591 0.3153 0.031 Uiso 1 1 calc R
H1B H -0.0623 0.3787 0.2955 0.031 Uiso 1 1 calc R
C2 C 0.0546(3) 0.37763(15) 0.38432(13) 0.0226(6) Uani 1 1 d .
H2A H -0.0083 0.3414 0.409 0.027 Uiso 1 1 calc R
C3 C 0.1184(3) 0.43554(14) 0.43518(13) 0.0216(6) Uani 1 1 d .
C4 C -0.0135(3) 0.48313(16) 0.46639(14) 0.0273(7) Uani 1 1 d .
H4A H -0.0912 0.4487 0.4831 0.033 Uiso 1 1 calc R
H4B H 0.0279 0.5107 0.5038 0.033 Uiso 1 1 calc R
C5 C -0.0914(4) 0.53956(17) 0.42007(15) 0.0336(7) Uani 1 1 d .
H5A H -0.1227 0.5834 0.4456 0.04 Uiso 1 1 calc R
H5B H -0.0165 0.5565 0.3878 0.04 Uiso 1 1 calc R
C6 C -0.2317(4) 0.50886(18) 0.38352(16) 0.0363(7) Uani 1 1 d .
H6A H -0.3186 0.5069 0.4135 0.044 Uiso 1 1 calc R
H6B H -0.2579 0.543 0.3478 0.044 Uiso 1 1 calc R
C7 C -0.3214(3) 0.38345(19) 0.35587(15) 0.0320(7) Uani 1 1 d .
C8 C -0.3919(4) 0.2578(2) 0.32560(19) 0.0470(9) Uani 1 1 d .
H8A H -0.486 0.2736 0.3474 0.056 Uiso 1 1 calc R
H8B H -0.3578 0.2109 0.3457 0.056 Uiso 1 1 calc R
C9 C -0.4227(7) 0.2452(3) 0.2535(3) 0.0843(16) Uani 1 1 d .
H9A H -0.3358 0.24 0.2271 0.101 Uiso 1 1 calc R
C10 C -0.5436(8) 0.2410(3) 0.2253(2) 0.0815(15) Uani 1 1 d .
H10A H -0.6351 0.2457 0.2488 0.098 Uiso 1 1 calc R
H10B H -0.5459 0.2329 0.18 0.098 Uiso 1 1 calc R
C11 C 0.1800(3) 0.33166(15) 0.34833(14) 0.0263(6) Uani 1 1 d .
H11A H 0.2383 0.3647 0.3202 0.039 Uiso 1 1 calc R
H11B H 0.1324 0.2929 0.3222 0.039 Uiso 1 1 calc R
H11C H 0.2473 0.3088 0.3802 0.039 Uiso 1 1 calc R
C12 C 0.3062(3) 0.54160(15) 0.43360(15) 0.0249(7) Uani 1 1 d .
C13 C 0.3915(3) 0.59628(15) 0.39060(15) 0.0301(7) Uani 1 1 d .
H13A H 0.3328 0.642 0.3863 0.045 Uiso 1 1 calc R
H13B H 0.4071 0.5743 0.3478 0.045 Uiso 1 1 calc R
H13C H 0.4895 0.6076 0.4102 0.045 Uiso 1 1 calc R
C14 C 0.1946(3) 0.39086(14) 0.49118(13) 0.0223(6) Uani 1 1 d .
C15 C 0.4266(3) 0.33599(15) 0.53969(13) 0.0239(6) Uani 1 1 d .
H15A H 0.3758 0.2869 0.5451 0.029 Uiso 1 1 calc R
C16 C 0.5941(3) 0.32129(17) 0.52053(15) 0.0300(7) Uani 1 1 d .
H16A H 0.5974 0.2893 0.4822 0.045 Uiso 1 1 calc R
H16B H 0.6463 0.2968 0.5564 0.045 Uiso 1 1 calc R
H16C H 0.644 0.3685 0.5109 0.045 Uiso 1 1 calc R
C17 C 0.4202(3) 0.37713(15) 0.60579(14) 0.0258(6) Uani 1 1 d .
C18 C 0.3827(3) 0.49522(16) 0.66529(14) 0.0281(7) Uani 1 1 d .
H18A H 0.4638 0.4778 0.6953 0.034 Uiso 1 1 calc R
C19 C 0.4094(4) 0.57897(17) 0.65177(15) 0.0381(8) Uani 1 1 d .
H19A H 0.5128 0.5864 0.6364 0.057 Uiso 1 1 calc R
H19B H 0.3939 0.6073 0.6917 0.057 Uiso 1 1 calc R
H19C H 0.3382 0.5961 0.6187 0.057 Uiso 1 1 calc R
C20 C 0.2270(4) 0.48623(16) 0.70083(14) 0.0304(7) Uani 1 1 d .
C21 C -0.0520(4) 0.4630(2) 0.69238(15) 0.0382(8) Uani 1 1 d .
H21A H -0.0489 0.4411 0.7368 0.046 Uiso 1 1 calc R
C22 C -0.1104(5) 0.5422(2) 0.6980(2) 0.0656(12) Uani 1 1 d .
H22A H -0.0397 0.5717 0.7237 0.098 Uiso 1 1 calc R
H22B H -0.2094 0.542 0.7191 0.098 Uiso 1 1 calc R
H22C H -0.1197 0.5639 0.6547 0.098 Uiso 1 1 calc R
C23 C -0.1529(4) 0.4135(2) 0.65018(19) 0.0459(9) Uani 1 1 d .
H23A H -0.1535 0.4324 0.6058 0.069 Uiso 1 1 calc R
H23B H -0.2559 0.4137 0.6674 0.069 Uiso 1 1 calc R
H23C H -0.1136 0.3627 0.6505 0.069 Uiso 1 1 calc R
C24 C 0.4605(6) 0.7755(2) 0.6274(2) 0.0605(11) Uani 1 1 d .
C25 C 0.5004(7) 0.7997(3) 0.6951(2) 0.0803(15) Uani 1 1 d .
H25A H 0.4078 0.8106 0.7192 0.12 Uiso 1 1 calc R
H25B H 0.5633 0.8444 0.6932 0.12 Uiso 1 1 calc R
H25C H 0.5559 0.76 0.717 0.12 Uiso 1 1 calc R
C26 C 0.5584(6) 0.7313(3) 0.5257(2) 0.0729(13) Uani 1 1 d .
H26A H 0.4677 0.6993 0.5249 0.087 Uiso 1 1 calc R
H26B H 0.6456 0.7007 0.5121 0.087 Uiso 1 1 calc R
C27 C 0.5375(8) 0.7941(3) 0.4773(3) 0.0864(16) Uani 1 1 d .
H27A H 0.4424 0.8198 0.4862 0.13 Uiso 1 1 calc R
H27B H 0.5351 0.7737 0.4333 0.13 Uiso 1 1 calc R
H27C H 0.6215 0.8291 0.4811 0.13 Uiso 1 1 calc R
N1 N -0.2040(3) 0.43352(13) 0.35681(12) 0.0292(6) Uani 1 1 d .
N2 N 0.2291(3) 0.48590(12) 0.40244(12) 0.0213(5) Uani 1 1 d .
N3 N 0.3473(3) 0.37680(13) 0.48717(13) 0.0220(5) Uani 1 1 d .
N4 N 0.3943(3) 0.45218(14) 0.60550(14) 0.0253(6) Uani 1 1 d .
N5 N 0.1067(3) 0.46300(15) 0.66580(13) 0.0305(6) Uani 1 1 d .
O1 O -0.4531(2) 0.39812(13) 0.37335(11) 0.0405(6) Uani 1 1 d .
O2 O -0.2749(2) 0.31530(13) 0.33408(12) 0.0403(6) Uani 1 1 d .
O3 O 0.3045(2) 0.54840(10) 0.49441(9) 0.0290(5) Uani 1 1 d .
O4 O 0.1177(2) 0.36790(10) 0.53806(9) 0.0254(5) Uani 1 1 d .
O5 O 0.4421(2) 0.34151(11) 0.65689(10) 0.0332(5) Uani 1 1 d .
O6 O 0.2184(3) 0.50419(14) 0.75958(10) 0.0440(6) Uani 1 1 d .
O7 O 0.3310(4) 0.77232(17) 0.60566(15) 0.0678(8) Uani 1 1 d .
O8 O 0.5834(4) 0.75688(18) 0.59178(17) 0.0732(9) 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 113.9(2)
C1 C2 C11 108.3(2)
C1 C2 C3 113.3(2)
C11 C2 C3 114.1(2)
N2 C3 C14 111.3(2)
N2 C3 C2 109.5(2)
C14 C3 C2 107.8(2)
N2 C3 C4 109.8(2)
C14 C3 C4 107.2(2)
C2 C3 C4 111.2(2)
C5 C4 C3 115.4(2)
C6 C5 C4 114.8(3)
N1 C6 C5 111.9(2)
O1 C7 O2 124.4(3)
O1 C7 N1 124.2(3)
O2 C7 N1 111.4(2)
O2 C8 C9 110.2(3)
C10 C9 C8 129.0(5)
O3 C12 N2 122.1(3)
O3 C12 C13 121.5(3)
N2 C12 C13 116.4(3)
O4 C14 N3 121.2(3)
O4 C14 C3 120.5(2)
N3 C14 C3 118.3(3)
N3 C15 C17 112.8(2)
N3 C15 C16 110.4(2)
C17 C15 C16 109.8(2)
O5 C17 N4 122.4(3)
O5 C17 C15 119.4(2)
N4 C17 C15 118.2(2)
N4 C18 C19 110.7(3)
N4 C18 C20 113.7(2)
C19 C18 C20 108.5(3)
O6 C20 N5 123.1(3)
O6 C20 C18 118.5(3)
N5 C20 C18 118.2(2)
N5 C21 C22 110.1(3)
N5 C21 C23 109.6(3)
C22 C21 C23 113.0(3)
O7 C24 O8 122.6(4)
O7 C24 C25 124.7(5)
O8 C24 C25 112.7(5)
O8 C26 C27 113.5(4)
C7 N1 C6 118.6(3)
C7 N1 C1 121.6(2)
C6 N1 C1 119.7(2)
C12 N2 C3 123.8(2)
C14 N3 C15 120.7(3)
C17 N4 C18 122.1(3)
C20 N5 C21 122.6(3)
C7 O2 C8 117.2(2)
C24 O8 C26 117.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.463(4)
C1 C2 1.539(4)
C2 C11 1.542(4)
C2 C3 1.555(4)
C3 N2 1.469(4)
C3 C14 1.533(4)
C3 C4 1.556(4)
C4 C5 1.527(4)
C5 C6 1.526(5)
C6 N1 1.457(4)
C7 O1 1.225(4)
C7 O2 1.345(4)
C7 N1 1.350(4)
C8 O2 1.447(4)
C8 C9 1.502(7)
C9 C10 1.197(7)
C12 O3 1.238(4)
C12 N2 1.347(4)
C12 C13 1.498(4)
C14 O4 1.230(3)
C14 N3 1.352(4)
C15 N3 1.458(4)
C15 C17 1.525(4)
C15 C16 1.529(4)
C17 O5 1.227(3)
C17 N4 1.345(4)
C18 N4 1.434(4)
C18 C19 1.523(4)
C18 C20 1.541(4)
C20 O6 1.234(4)
C20 N5 1.329(4)
C21 N5 1.480(4)
C21 C22 1.494(5)
C21 C23 1.505(5)
C24 O7 1.209(6)
C24 O8 1.330(6)
C24 C25 1.480(6)
C26 O8 1.430(6)
C26 C27 1.493(7)
