#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:43:39 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243560 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/62/1556205.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_1556205
loop_
_publ_author_name
'Brawn, Ryan A.'
'Guimarães, Cristiano R W'
'McClure, Kim F.'
'Liras, Spiros'
_publ_section_title
;
 Enantioselective hydroarylation of bridged [3.2.1] heterocycles: an
 efficient entry into the homoepibatidine skeleton.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3424
_journal_page_last               3427
_journal_paper_doi               10.1021/ol401477r
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H21 Cl N2 O3'
_chemical_formula_weight         324.80
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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                   9.8721(7)
_cell_length_b                   10.1397(7)
_cell_length_c                   16.1579(12)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.58
_cell_measurement_theta_min      2.37
_cell_volume                     1617.4(2)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω 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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            46801
_diffrn_reflns_theta_full        31.50
_diffrn_reflns_theta_max         31.50
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.9332
_exptl_absorpt_correction_T_min  0.9220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         5389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.2576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0742
_reflns_number_gt                5265
_reflns_number_total             5389
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401477r_si_003.cif
_cod_data_source_block           sfy15
_cod_database_code               1556205
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
Cl1 Cl 0.79091(3) 0.84094(2) 0.565678(15) 0.02268(6) Uani 1 1 d .
O1 O 0.79798(8) 0.06400(7) 0.33117(4) 0.01984(14) Uani 1 1 d .
O2 O 1.20772(7) 0.24553(8) 0.29086(4) 0.01707(13) Uani 1 1 d .
O3 O 1.19297(7) 0.25767(7) 0.43230(4) 0.01752(13) Uani 1 1 d .
N1 N 1.00600(8) 0.25609(10) 0.35066(5) 0.01675(15) Uani 1 1 d .
N2 N 0.68230(8) 0.62095(9) 0.51447(5) 0.01690(15) Uani 1 1 d .
C1 C 0.78828(9) 0.32743(9) 0.38568(5) 0.01307(14) Uani 1 1 d .
H1 H 0.6990 0.2853 0.3981 0.016 Uiso 1 1 calc R
C2 C 0.90366(9) 0.23514(9) 0.41496(5) 0.01370(15) Uani 1 1 d .
H2 H 0.9377 0.2592 0.4713 0.016 Uiso 1 1 calc R
C3 C 0.85692(10) 0.09160(10) 0.41041(6) 0.01780(17) Uani 1 1 d .
H3A H 0.9352 0.0324 0.4197 0.021 Uiso 1 1 calc R
H3B H 0.7894 0.0746 0.4544 0.021 Uiso 1 1 calc R
C4 C 0.88759(11) 0.09862(11) 0.26523(6) 0.02008(19) Uani 1 1 d .
H4A H 0.8414 0.0849 0.2115 0.024 Uiso 1 1 calc R
H4B H 0.9684 0.0408 0.2668 0.024 Uiso 1 1 calc R
C5 C 0.93174(9) 0.24262(11) 0.27258(6) 0.01630(17) Uani 1 1 d .
H5 H 0.9860 0.2726 0.2238 0.020 Uiso 1 1 calc R
C6 C 0.80894(9) 0.33275(10) 0.28958(5) 0.01542(15) Uani 1 1 d .
H6A H 0.7275 0.2999 0.2604 0.019 Uiso 1 1 calc R
H6B H 0.8276 0.4241 0.2712 0.019 Uiso 1 1 calc R
C7 C 1.14148(9) 0.25208(9) 0.36386(5) 0.01319(15) Uani 1 1 d .
C8 C 1.35724(9) 0.24954(11) 0.28848(6) 0.01626(16) Uani 1 1 d .
C9 C 1.38549(10) 0.24559(13) 0.19590(6) 0.0250(2) Uani 1 1 d .
H9A H 1.3478 0.1644 0.1724 0.037 Uiso 1 1 calc R
H9B H 1.4835 0.2477 0.1865 0.037 Uiso 1 1 calc R
H9C H 1.3434 0.3221 0.1692 0.037 Uiso 1 1 calc R
C10 C 1.41553(11) 0.12903(11) 0.33192(7) 0.0228(2) Uani 1 1 d .
H10A H 1.3949 0.1337 0.3912 0.034 Uiso 1 1 calc R
H10B H 1.5139 0.1268 0.3241 0.034 Uiso 1 1 calc R
H10C H 1.3752 0.0490 0.3085 0.034 Uiso 1 1 calc R
C11 C 1.40792(10) 0.37875(10) 0.32528(7) 0.01957(18) Uani 1 1 d .
H11A H 1.3643 0.4529 0.2970 0.029 Uiso 1 1 calc R
H11B H 1.5063 0.3847 0.3182 0.029 Uiso 1 1 calc R
H11C H 1.3857 0.3817 0.3844 0.029 Uiso 1 1 calc R
C12 C 0.79495(9) 0.46019(9) 0.42759(5) 0.01397(14) Uani 1 1 d .
C13 C 0.68426(9) 0.50620(9) 0.47247(6) 0.01537(16) Uani 1 1 d .
H13 H 0.6049 0.4532 0.4736 0.018 Uiso 1 1 calc R
C14 C 0.91038(10) 0.53955(10) 0.42632(7) 0.01961(18) Uani 1 1 d .
H14 H 0.9884 0.5120 0.3965 0.024 Uiso 1 1 calc R
C15 C 0.91122(10) 0.65891(11) 0.46869(7) 0.02033(18) Uani 1 1 d .
H15 H 0.9883 0.7150 0.4686 0.024 Uiso 1 1 calc R
C16 C 0.79396(11) 0.69211(9) 0.51117(6) 0.01658(16) 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
C4 O1 C3 111.51(8)
C7 O2 C8 120.36(7)
C7 N1 C2 124.39(8)
C7 N1 C5 128.79(7)
C2 N1 C5 104.61(7)
C16 N2 C13 116.12(8)
C12 C1 C2 111.72(7)
C12 C1 C6 114.11(7)
C2 C1 C6 103.17(7)
N1 C2 C3 108.19(8)
N1 C2 C1 101.72(7)
C3 C2 C1 109.79(7)
O1 C3 C2 110.57(8)
O1 C4 C5 110.70(8)
N1 C5 C4 107.37(8)
N1 C5 C6 100.64(7)
C4 C5 C6 110.83(8)
C5 C6 C1 104.97(7)
O3 C7 O2 126.37(8)
O3 C7 N1 123.59(8)
O2 C7 N1 110.00(7)
O2 C8 C10 110.10(8)
O2 C8 C9 102.01(7)
C10 C8 C9 111.27(9)
O2 C8 C11 109.98(8)
C10 C8 C11 112.72(8)
C9 C8 C11 110.25(9)
C13 C12 C14 117.10(8)
C13 C12 C1 119.92(8)
C14 C12 C1 122.94(8)
N2 C13 C12 124.27(8)
C15 C14 C12 119.98(9)
C16 C15 C14 116.73(9)
N2 C16 C15 125.79(9)
N2 C16 Cl1 115.96(8)
C15 C16 Cl1 118.24(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C16 1.7475(9)
O1 C4 1.4286(13)
O1 C3 1.4339(12)
O2 C7 1.3502(10)
O2 C8 1.4771(11)
O3 C7 1.2184(11)
N1 C7 1.3551(11)
N1 C2 1.4647(11)
N1 C5 1.4654(11)
N2 C16 1.3185(13)
N2 C13 1.3471(13)
C1 C12 1.5084(12)
C1 C2 1.5482(13)
C1 C6 1.5670(12)
C2 C3 1.5286(14)
C4 C5 1.5284(15)
C5 C6 1.5429(13)
C8 C10 1.5221(15)
C8 C9 1.5222(14)
C8 C11 1.5233(14)
C12 C13 1.3920(12)
C12 C14 1.3951(12)
C14 C15 1.3906(14)
C15 C16 1.3873(14)
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
C4 H4A Cl1 0.99 2.80 3.7253(11) 156.3 2_664
C10 H10A O3 0.98 2.45 3.0263(13) 117.3 .
C11 H11C O3 0.98 2.41 3.0000(13) 118.3 .
C15 H15 N2 0.95 2.55 3.4954(13) 172.4 4_566
