#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:52:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178448 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/69/4026902.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_4026902
loop_
_publ_author_name
'Sara H. Kyne'
'Jonathan A. L. Miles'
'Jonathan M. Percy'
'Kuldip Singh'
_publ_section_title
;
 Executing and Rationalizing the Synthesis of a Difluorinated Analogue of
 a Ring-Expanded Calystegine B2
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              991
_journal_page_last               998
_journal_paper_doi               10.1021/jo2022845
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C15 H19 F2 N O3'
_chemical_formula_sum            'C15 H19 F2 N O3'
_chemical_formula_weight         299.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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            8
_cell_length_a                   11.428(3)
_cell_length_b                   24.352(6)
_cell_length_c                   10.474(2)
_cell_measurement_reflns_used    870
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.25
_cell_measurement_theta_min      2.77
_cell_volume                     2914.9(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19696
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
absorption correction based on 8492 reflections (SADABS); Rint 0.052 
before correction and 0.036 after.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0498
_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)+(0.0561P)²+0.9465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                2233
_reflns_number_total             2576
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2022845_si_003_2.cif
_cod_data_source_block           13a
_cod_original_cell_volume        2915.0(12)
_cod_database_code               4026902
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
F1 F 1.12653(9) 0.54295(5) 0.14552(10) 0.0245(3) Uani 1 1 d .
F2 F 1.10207(10) 0.63133(5) 0.16281(11) 0.0289(3) Uani 1 1 d .
N1 N 0.88462(14) 0.52827(7) 0.09372(15) 0.0189(4) Uani 1 1 d .
H1 H 0.8315(19) 0.5244(8) 0.033(2) 0.024(6) Uiso 1 1 d .
O1 O 1.00129(12) 0.57733(7) -0.04978(12) 0.0224(3) Uani 1 1 d .
H1A H 1.031(2) 0.5444(11) -0.057(2) 0.039(7) Uiso 1 1 d .
O2 O 1.10191(12) 0.55756(6) 0.39211(13) 0.0230(3) Uani 1 1 d .
O3 O 0.86078(13) 0.52943(7) 0.44340(13) 0.0269(4) Uani 1 1 d .
H3 H 0.889(2) 0.5032(11) 0.493(3) 0.053(8) Uiso 1 1 d .
C1 C 0.94818(17) 0.57942(8) 0.07082(18) 0.0192(4) Uani 1 1 d .
C2 C 1.04443(17) 0.58221(8) 0.17442(19) 0.0193(4) Uani 1 1 d .
C3 C 1.00628(17) 0.57356(8) 0.31318(18) 0.0188(4) Uani 1 1 d .
H3A H 0.9715 0.6083 0.3469 0.023 Uiso 1 1 calc R
C4 C 0.91624(17) 0.52768(8) 0.32172(17) 0.0199(4) Uani 1 1 d .
H4 H 0.9582 0.4918 0.3139 0.024 Uiso 1 1 calc R
C5 C 0.82281(17) 0.53030(8) 0.21757(18) 0.0209(5) Uani 1 1 d .
H5 H 0.7754 0.4959 0.2243 0.025 Uiso 1 1 calc R
C6 C 0.73728(18) 0.57845(9) 0.22540(19) 0.0267(5) Uani 1 1 d .
H6A H 0.6710 0.5713 0.1668 0.032 Uiso 1 1 calc R
H6B H 0.7055 0.5804 0.3132 0.032 Uiso 1 1 calc R
C7 C 0.79170(18) 0.63391(9) 0.19157(19) 0.0277(5) Uani 1 1 d .
H7A H 0.8397 0.6470 0.2641 0.033 Uiso 1 1 calc R
H7B H 0.7288 0.6611 0.1765 0.033 Uiso 1 1 calc R
C8 C 0.86845(18) 0.62956(9) 0.07222(19) 0.0247(5) Uani 1 1 d .
H8A H 0.8173 0.6283 -0.0040 0.030 Uiso 1 1 calc R
H8B H 0.9173 0.6630 0.0658 0.030 Uiso 1 1 calc R
C9 C 1.18437(18) 0.60021(9) 0.4261(2) 0.0258(5) Uani 1 1 d .
H9A H 1.2170 0.6163 0.3470 0.031 Uiso 1 1 calc R
H9B H 1.2499 0.5835 0.4743 0.031 Uiso 1 1 calc R
C10 C 1.13176(17) 0.64533(9) 0.50505(19) 0.0242(5) Uani 1 1 d .
C11 C 1.1303(2) 0.69866(10) 0.4617(2) 0.0370(6) Uani 1 1 d .
H11 H 1.1609 0.7069 0.3796 0.044 Uiso 1 1 calc R
C12 C 1.0849(3) 0.74037(10) 0.5363(3) 0.0478(7) Uani 1 1 d .
H12 H 1.0854 0.7771 0.5059 0.057 Uiso 1 1 calc R
C13 C 1.0390(2) 0.72872(10) 0.6545(2) 0.0422(6) Uani 1 1 d .
H13 H 1.0072 0.7574 0.7053 0.051 Uiso 1 1 calc R
C14 C 1.0391(2) 0.67560(10) 0.6996(2) 0.0372(6) Uani 1 1 d .
H14 H 1.0070 0.6674 0.7811 0.045 Uiso 1 1 calc R
C15 C 1.0862(2) 0.63425(9) 0.6251(2) 0.0328(5) Uani 1 1 d .
H15 H 1.0875 0.5977 0.6567 0.039 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 0.0033 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'
F F 0.0171 0.0103 '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
C1 N1 C5 110.68(15)
C1 N1 H1 108.4(14)
C5 N1 H1 107.6(14)
C1 O1 H1A 106.5(16)
C3 O2 C9 116.50(15)
C4 O3 H3 109.8(18)
O1 C1 N1 109.39(15)
O1 C1 C8 107.26(16)
N1 C1 C8 112.59(16)
O1 C1 C2 109.01(16)
N1 C1 C2 106.00(15)
C8 C1 C2 112.54(16)
F2 C2 F1 105.04(15)
F2 C2 C3 109.93(15)
F1 C2 C3 107.92(15)
F2 C2 C1 108.53(15)
F1 C2 C1 107.50(15)
C3 C2 C1 117.21(16)
O2 C3 C4 106.49(15)
O2 C3 C2 111.71(16)
C4 C3 C2 110.44(15)
O2 C3 H3A 109.4
C4 C3 H3A 109.4
C2 C3 H3A 109.4
O3 C4 C3 109.37(15)
O3 C4 C5 109.07(16)
C3 C4 C5 113.58(16)
O3 C4 H4 108.2
C3 C4 H4 108.2
C5 C4 H4 108.2
N1 C5 C4 106.93(15)
N1 C5 C6 112.23(16)
C4 C5 C6 116.15(16)
N1 C5 H5 107.0
C4 C5 H5 107.0
C6 C5 H5 107.0
C7 C6 C5 113.90(17)
C7 C6 H6A 108.8
C5 C6 H6A 108.8
C7 C6 H6B 108.8
C5 C6 H6B 108.8
H6A C6 H6B 107.7
C6 C7 C8 111.18(17)
C6 C7 H7A 109.4
C8 C7 H7A 109.4
C6 C7 H7B 109.4
C8 C7 H7B 109.4
H7A C7 H7B 108.0
C1 C8 C7 113.96(17)
C1 C8 H8A 108.8
C7 C8 H8A 108.8
C1 C8 H8B 108.8
C7 C8 H8B 108.8
H8A C8 H8B 107.7
O2 C9 C10 113.60(17)
O2 C9 H9A 108.8
C10 C9 H9A 108.8
O2 C9 H9B 108.8
C10 C9 H9B 108.8
H9A C9 H9B 107.7
C11 C10 C15 118.6(2)
C11 C10 C9 120.9(2)
C15 C10 C9 120.5(2)
C10 C11 C12 120.7(2)
C10 C11 H11 119.6
C12 C11 H11 119.6
C13 C12 C11 120.1(2)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C14 120.2(2)
C12 C13 H13 119.9
C14 C13 H13 119.9
C13 C14 C15 119.4(2)
C13 C14 H14 120.3
C15 C14 H14 120.3
C14 C15 C10 121.1(2)
C14 C15 H15 119.5
C10 C15 H15 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.373(2)
F2 C2 1.371(2)
N1 C1 1.462(3)
N1 C5 1.478(2)
N1 H1 0.88(2)
O1 C1 1.402(2)
O1 H1A 0.88(3)
O2 C3 1.425(2)
O2 C9 1.447(2)
O3 C4 1.424(2)
O3 H3 0.88(3)
C1 C8 1.523(3)
C1 C2 1.547(3)
C2 C3 1.532(3)
C3 C4 1.522(3)
C3 H3A 1.0000
C4 C5 1.528(3)
C4 H4 1.0000
C5 C6 1.529(3)
C5 H5 1.0000
C6 C7 1.528(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.531(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.501(3)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.376(3)
C10 C15 1.388(3)
C11 C12 1.383(3)
C11 H11 0.9500
C12 C13 1.374(4)
C12 H12 0.9500
C13 C14 1.377(3)
C13 H13 0.9500
C14 C15 1.383(3)
C14 H14 0.9500
C15 H15 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N1 0.88(3) 2.05(3) 2.920(2) 172(2) 5_765
N1 H1 F1 0.88(2) 2.54(2) 3.050(2) 117.9(17) 5_765
O3 H3 O2 0.88(3) 1.91(3) 2.764(2) 161(3) 5_766
N1 H1 O3 0.88(2) 2.39(2) 3.216(2) 155.4(18) 8_755
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
C5 N1 C1 O1 -177.22(15)
C5 N1 C1 C8 -58.1(2)
C5 N1 C1 C2 65.38(19)
O1 C1 C2 F2 66.34(19)
N1 C1 C2 F2 -176.01(14)
C8 C1 C2 F2 -52.5(2)
O1 C1 C2 F1 -46.8(2)
N1 C1 C2 F1 70.87(18)
C8 C1 C2 F1 -165.64(15)
O1 C1 C2 C3 -168.45(16)
N1 C1 C2 C3 -50.8(2)
C8 C1 C2 C3 72.7(2)
C9 O2 C3 C4 -164.36(15)
C9 O2 C3 C2 75.0(2)
F2 C2 C3 O2 -76.45(19)
F1 C2 C3 O2 37.6(2)
C1 C2 C3 O2 159.04(16)
F2 C2 C3 C4 165.22(15)
F1 C2 C3 C4 -80.73(18)
C1 C2 C3 C4 40.7(2)
O2 C3 C4 O3 73.04(19)
C2 C3 C4 O3 -165.50(15)
O2 C3 C4 C5 -164.87(15)
C2 C3 C4 C5 -43.4(2)
C1 N1 C5 C4 -70.60(19)
C1 N1 C5 C6 57.9(2)
O3 C4 C5 N1 -179.91(15)
C3 C4 C5 N1 57.8(2)
O3 C4 C5 C6 53.9(2)
C3 C4 C5 C6 -68.3(2)
N1 C5 C6 C7 -51.9(2)
C4 C5 C6 C7 71.5(2)
C5 C6 C7 C8 44.3(2)
O1 C1 C8 C7 172.70(16)
N1 C1 C8 C7 52.3(2)
C2 C1 C8 C7 -67.4(2)
C6 C7 C8 C1 -44.4(2)
C3 O2 C9 C10 63.5(2)
O2 C9 C10 C11 -119.1(2)
O2 C9 C10 C15 62.6(3)
C15 C10 C11 C12 0.3(3)
C9 C10 C11 C12 -178.1(2)
C10 C11 C12 C13 -0.9(4)
C11 C12 C13 C14 0.6(4)
C12 C13 C14 C15 0.4(4)
C13 C14 C15 C10 -1.0(4)
C11 C10 C15 C14 0.7(3)
C9 C10 C15 C14 179.0(2)
