#------------------------------------------------------------------------------
#$Date: 2016-03-22 22:00:52 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179030 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/28/4122882.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_4122882
loop_
_publ_author_name
'Parra, Alejandro'
'Amenós, Laura'
'Guisán-Ceinos, Manuel'
'López, Aurora'
'García Ruano, José Luis'
'Tortosa, Mariola'
_publ_section_title
;
 Copper-Catalyzed Diastereo- and Enantioselective Desymmetrization of
 Cyclopropenes: Synthesis of Cyclopropylboronates.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141031133923007
_journal_paper_doi               10.1021/ja510419z
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H14 Cl N O4'
_chemical_formula_weight         331.74
_chemical_name_common            MGC-109
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1340(2)
_cell_length_b                   10.6384(3)
_cell_length_c                   21.0677(7)
_cell_measurement_reflns_used    8781
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      24.3962
_cell_measurement_theta_min      2.7212
_cell_volume                     1598.92(8)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24711
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.237
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0423
_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)+(0.0907P)²+0.2539P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                2399
_reflns_number_total             2935
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja510419z_si_003.cif
_cod_data_source_block           I
_cod_database_code               4122882
loop_
_space_group_symop_operation_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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.4579(4) 0.4062(2) 0.13834(13) 0.0582(7) Uani d . 1
C C2 0.4517(5) 0.4586(2) 0.07913(13) 0.0615(7) Uani d . 1
H H2 0.4493 0.4081 0.0431 0.074 Uiso calc R 1
C C3 0.4491(5) 0.5884(2) 0.07369(12) 0.0568(7) Uani d . 1
H H3 0.4455 0.6246 0.0335 0.068 Uiso calc R 1
C C4 0.4517(4) 0.6654(2) 0.12630(12) 0.0534(6) Uani d . 1
C C5 0.4577(6) 0.6085(3) 0.18514(14) 0.0740(9) Uani d . 1
H H5 0.4602 0.6582 0.2214 0.089 Uiso calc R 1
C C6 0.4600(6) 0.4791(3) 0.19123(14) 0.0738(9) Uani d . 1
H H6 0.4631 0.4423 0.2313 0.089 Uiso calc R 1
C C7 0.4540(5) 0.8068(2) 0.11881(12) 0.0559(6) Uani d . 1
C C8 0.2988(6) 0.8845(3) 0.14779(16) 0.0783(10) Uani d . 1
H H8A 0.2045 0.841 0.1727 0.094 Uiso calc R 1
H H8B 0.3297 0.9683 0.1626 0.094 Uiso calc R 1
C C9 0.3027(5) 0.8618(3) 0.08016(15) 0.0649(8) Uani d . 1
H H9 0.209 0.802 0.0644 0.078 Uiso calc R 1
C C10 0.6450(5) 0.8648(3) 0.1176(2) 0.0832(11) Uani d . 1
H H10A 0.7082 0.8475 0.1569 0.125 Uiso calc R 1
H H10B 0.6337 0.9541 0.1121 0.125 Uiso calc R 1
H H10C 0.7159 0.8302 0.0831 0.125 Uiso calc R 1
C C11 0.4119(5) 0.9305(3) -0.01921(14) 0.0613(8) Uani d . 1
C C12 0.4366(4) 1.0378(2) -0.06348(12) 0.0543(7) Uani d . 1
C C13 0.4281(6) 1.1630(3) -0.04474(14) 0.0698(9) Uani d . 1
H H13 0.4098 1.1829 -0.0022 0.084 Uiso calc R 1
C C14 0.4466(5) 1.2570(2) -0.08855(14) 0.0677(8) Uani d . 1
H H14 0.4435 1.3409 -0.0762 0.081 Uiso calc R 1
C C15 0.4698(4) 1.2249(2) -0.15137(12) 0.0549(6) Uani d . 1
C C16 0.4781(4) 1.1024(3) -0.17140(12) 0.0574(7) Uani d . 1
H H16 0.4944 1.0832 -0.2141 0.069 Uiso calc R 1
C C17 0.4617(4) 1.0087(2) -0.12682(12) 0.0561(7) Uani d . 1
H H17 0.4676 0.925 -0.1394 0.067 Uiso calc R 1
Cl Cl1 0.46233(13) 0.24232(7) 0.14510(4) 0.0775(3) Uani d . 1
N N1 0.4853(4) 1.3261(2) -0.19877(13) 0.0686(7) Uani d . 1
O O1 0.3435(3) 0.96580(16) 0.03842(9) 0.0665(6) Uani d . 1
O O2 0.4442(4) 0.82387(17) -0.03288(10) 0.0704(6) Uani d . 1
O O3 0.4558(5) 1.4323(2) -0.18235(12) 0.0975(9) Uani d . 1
O O4 0.5295(6) 1.2967(3) -0.25255(12) 0.1107(10) Uani d . 1
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
C6 C1 C2 121.1(2)
C6 C1 Cl1 120.2(2)
C2 C1 Cl1 118.8(2)
C1 C2 C3 118.8(2)
C1 C2 H2 120.6
C3 C2 H2 120.6
C4 C3 C2 121.7(2)
C4 C3 H3 119.2
C2 C3 H3 119.2
C3 C4 C5 117.6(2)
C3 C4 C7 120.4(2)
C5 C4 C7 122.0(2)
C6 C5 C4 121.4(3)
C6 C5 H5 119.3
C4 C5 H5 119.3
C1 C6 C5 119.5(3)
C1 C6 H6 120.3
C5 C6 H6 120.3
C9 C7 C10 119.6(3)
C9 C7 C8 57.9(2)
C10 C7 C8 116.6(3)
C9 C7 C4 116.4(3)
C10 C7 C4 115.0(3)
C8 C7 C4 119.6(3)
C9 C8 C7 59.8(2)
C9 C8 H8A 117.8
C7 C8 H8A 117.8
C9 C8 H8B 117.8
C7 C8 H8B 117.8
H8A C8 H8B 114.9
C8 C9 O1 118.5(3)
C8 C9 C7 62.3(2)
O1 C9 C7 119.6(3)
C8 C9 H9 115.4
O1 C9 H9 115.4
C7 C9 H9 115.4
C7 C10 H10A 109.5
C7 C10 H10B 109.5
H10A C10 H10B 109.5
C7 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O2 C11 O1 123.1(3)
O2 C11 C12 123.9(3)
O1 C11 C12 113.0(2)
C17 C12 C13 119.7(3)
C17 C12 C11 116.7(2)
C13 C12 C11 123.6(3)
C14 C13 C12 120.3(3)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 118.6(2)
C13 C14 H14 120.7
C15 C14 H14 120.7
C16 C15 C14 122.5(2)
C16 C15 N1 118.8(2)
C14 C15 N1 118.7(2)
C15 C16 C17 118.4(2)
C15 C16 H16 120.8
C17 C16 H16 120.8
C16 C17 C12 120.5(2)
C16 C17 H17 119.7
C12 C17 H17 119.7
O3 N1 O4 123.7(3)
O3 N1 C15 118.6(3)
O4 N1 C15 117.6(3)
C11 O1 C9 113.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.358(4)
C1 C2 1.367(4)
C1 Cl1 1.750(3)
C2 C3 1.386(3)
C2 H2 0.93
C3 C4 1.378(4)
C3 H3 0.93
C4 C5 1.380(4)
C4 C7 1.513(4)
C5 C6 1.382(4)
C5 H5 0.93
C6 H6 0.93
C7 C9 1.474(4)
C7 C10 1.496(5)
C7 C8 1.510(5)
C8 C9 1.445(5)
C8 H8A 0.97
C8 H8B 0.97
C9 O1 1.443(3)
C9 H9 0.98
C10 H10A 0.96
C10 H10B 0.96
C10 H10C 0.96
C11 O2 1.193(3)
C11 O1 1.362(4)
C11 C12 1.485(4)
C12 C17 1.382(4)
C12 C13 1.390(4)
C13 C14 1.367(4)
C13 H13 0.93
C14 C15 1.377(4)
C14 H14 0.93
C15 C16 1.371(4)
C15 N1 1.472(3)
C16 C17 1.375(4)
C16 H16 0.93
C17 H17 0.93
N1 O3 1.201(3)
N1 O4 1.217(4)
