#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:56:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180523 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/92/7219285.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_7219285
loop_
_publ_author_name
'Nonn, Melinda'
'Kiss, Lorand'
'Hänninen, Mikko'
'Fulop, Ferenc'
_publ_section_title
;
 An insight into the synthesis of novel aryl-substituted alicyclic
 β-amino acid derivatives through substrate-directed palladium-catalysed
 regio- and stereoselective cross-coupling
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA16196C
_journal_year                    2015
_chemical_formula_moiety         'C19 H25 N O4'
_chemical_formula_sum            'C19 H25 N O4'
_chemical_formula_weight         331.40
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2014-12-10 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.778(3)
_cell_length_b                   6.9181(14)
_cell_length_c                   17.853(4)
_cell_measurement_reflns_used    2457
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      0.41
_cell_measurement_wavelength     0.71073
_cell_volume                     1825.2(7)
_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_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            '95mm CCD camera on \k-goniostat'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      0.049678
_diffrn_orient_matrix_UB_12      -0.059198
_diffrn_orient_matrix_UB_13      0.019029
_diffrn_orient_matrix_UB_21      -0.075075
_diffrn_orient_matrix_UB_22      -0.032407
_diffrn_orient_matrix_UB_23      -0.039584
_diffrn_orient_matrix_UB_31      0.112816
_diffrn_orient_matrix_UB_32      0.004502
_diffrn_orient_matrix_UB_33      -0.034721
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3465
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.666
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1951
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      14.476
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0646P)²+0.8478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1478
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1585
_reflns_number_total             1951
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ra16196c2.cif
_cod_data_source_block           KLHN53
_cod_original_cell_volume        1825.2(6)
_cod_database_code               7219285
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H4 of C4, H19A of C19A, H20A of C20A, H21 of C21, H20B
  of C20B, {H19B,H8A,H8B} of C19B
 At 1.5 times of:
  {H16A,H16B,H16C} of C16, {H15A,H15B,H15C} of C15, {H9A,H9B,H9C} of C9, H11
  of C19B
2. Restrained distances
 N11-H11
 0.87 with sigma of 0.005
 C9-C8
 1.54 with sigma of 0.01
 H8B-C8 = H8B-H8A
 0.99 with sigma of 0.001
 C18-C19A = C19A-C20A = C20A-C21 = C21-C20B_$1 = C20B_$1-C19B_$1 = C19B_$1-C18
 = C18-C19B = C19B-C20B
 1.39 with sigma of 0.005
 H8A-H8B
 1.615 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C18 \\sim C19A \\sim C20A \\sim C21 \\sim C20B \\sim C19B: within 2A with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C20B) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 Fixed Sof: H5B(0.5) H5A(0.5) H3A(0.5) H3B(0.5) H16A(0.5) H16B(0.5) H16C(0.5)
 C8(0.5) C19A(0.5) H19A(0.5) C4(0.5) H4(0.5) C20A(0.5) H20A(0.5) C9(0.5)
 H9A(0.5) H9B(0.5) H9C(0.5) C21(0.5) H21(0.5) C20B(0.5) H20B(0.5) C19B(0.5)
 H19B(0.5) H8B(0.5)
5.a Ternary CH refined with riding coordinates:
 C4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5B,H5A), C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 C19A(H19A), C20A(H20A), C21(H21), C20B(H20B), C19B(H19B)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C9(H9A,H9B,H9C)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O13 O 0.32623(10) 0.2500 0.63618(9) 0.0415(5) Uani 1 2 d S T P . .
O17 O 0.46680(11) 0.2500 0.68910(10) 0.0503(5) Uani 1 2 d S T P . .
N11 N 0.44310(13) 0.2500 0.56186(11) 0.0381(5) Uani 1 2 d DS T P . .
O10 O 0.39586(12) 0.2500 0.41496(11) 0.0673(7) Uani 1 2 d S T P . .
C5 C 0.64706(16) 0.2500 0.44397(13) 0.0415(6) Uani 1 2 d S T P . .
H5B H 0.6697 0.3821 0.4337 0.050 Uiso 0.5 1 calc R . . . .
H5A H 0.6628 0.1645 0.4014 0.050 Uiso 0.5 1 calc R . . . .
O7 O 0.51074(12) 0.2500 0.33277(9) 0.0553(6) Uani 1 2 d S T P . .
C12 C 0.41721(16) 0.2500 0.63577(13) 0.0365(5) Uani 1 2 d S T P . .
C1 C 0.54684(15) 0.2500 0.45865(13) 0.0357(5) Uani 1 2 d S T P . .
C3 C 0.61395(17) 0.2500 0.57898(14) 0.0489(7) Uani 1 2 d S T P . .
H3A H 0.6084 0.1637 0.6230 0.059 Uiso 0.5 1 calc R . . . .
H3B H 0.6299 0.3819 0.5960 0.059 Uiso 0.5 1 calc R . . . .
C2 C 0.52933(15) 0.2500 0.53291(13) 0.0357(5) Uani 1 2 d S T P . .
C6 C 0.47707(17) 0.2500 0.40230(14) 0.0447(6) Uani 1 2 d S T P . .
C16 C 0.17741(18) 0.2500 0.67799(17) 0.0743(11) Uani 1 2 d S T P . .
H16A H 0.1354 0.2613 0.7202 0.111 Uiso 0.5 1 calc GR . . A -1
H16B H 0.1657 0.1291 0.6511 0.111 Uiso 0.5 1 calc GR . . A -1
H16C H 0.1688 0.3596 0.6440 0.111 Uiso 0.5 1 calc GR . . A -1
C15 C 0.29400(15) 0.0686(4) 0.75047(12) 0.0637(6) Uani 1 1 d . . . . .
H15A H 0.2527 0.0595 0.7933 0.096 Uiso 1 1 calc GR . . . .
H15B H 0.3566 0.0724 0.7685 0.096 Uiso 1 1 calc GR . . . .
H15C H 0.2858 -0.0442 0.7180 0.096 Uiso 1 1 calc GR . . . .
C14 C 0.27392(16) 0.2500 0.70693(13) 0.0434(6) Uani 1 2 d S T P . .
C18 C 0.78098(17) 0.2500 0.53658(14) 0.0538(7) Uani 1 2 d DS TU P . .
C8 C 0.4455(2) 0.2021(7) 0.2723(2) 0.0555(17) Uani 0.5 1 d D U . . .
C19A C 0.8024(3) 0.4428(6) 0.5360(3) 0.0660(10) Uani 0.5 1 d D U . B 1
H19A H 0.7552 0.5326 0.5264 0.079 Uiso 0.5 1 calc R . . B 1
C4 C 0.6856(2) 0.1693(6) 0.52007(18) 0.0446(9) Uani 0.5 1 d . . . B .
H4 H 0.6860 0.0247 0.5200 0.054 Uiso 0.5 1 calc R . . . .
C20A C 0.8878(3) 0.5145(8) 0.5483(3) 0.0765(11) Uani 0.5 1 d D U . B 1
H20A H 0.8997 0.6490 0.5442 0.092 Uiso 0.5 1 calc R . . B 1
C9 C 0.4850(3) 0.2929(11) 0.20337(18) 0.059(2) Uani 0.5 1 d D U . . .
H9A H 0.4944 0.4313 0.2121 0.089 Uiso 0.5 1 calc GR . . . .
H9B H 0.4433 0.2752 0.1612 0.089 Uiso 0.5 1 calc GR . . . .
H9C H 0.5430 0.2314 0.1917 0.089 Uiso 0.5 1 calc GR . . . .
C21 C 0.9546(3) 0.3893(7) 0.5665(4) 0.0709(13) Uani 0.5 1 d D U . B 1
H21 H 1.0099 0.4476 0.5816 0.085 Uiso 0.5 1 calc R . . B 1
C20B C 0.9386(3) 0.3059(6) 0.5687(3) 0.0621(12) Uani 0.5 1 d D U . B 2
H20B H 0.9903 0.3843 0.5775 0.074 Uiso 0.5 1 calc R . . B 2
C19B C 0.8515(2) 0.3762(7) 0.5539(3) 0.0703(10) Uani 0.5 1 d D U . B 2
H19B H 0.8404 0.5114 0.5557 0.084 Uiso 0.5 1 calc R . . B 2
H8A H 0.386(2) 0.2500 0.285(2) 0.084 Uiso 1 2 d DRS T P . .
H8B H 0.4433(19) 0.0595(9) 0.268(3) 0.084 Uiso 0.5 1 d DR . . . .
H11 H 0.402(2) 0.2500 0.5272(16) 0.106 Uiso 1 2 d DRS T P . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C12 O13 C14 121.78(18) . .
C12 N11 C2 128.2(2) . .
C12 N11 H11 119(3) . .
C2 N11 H11 113(3) . .
H5B C5 H5A 109.3 . .
C1 C5 H5B 111.4 . .
C1 C5 H5A 111.4 . .
C1 C5 C4 101.87(19) . .
C4 C5 H5B 111.4 . .
C4 C5 H5A 111.4 . .
C6 O7 C8 115.7(2) . .
C6 O7 C8 115.7(2) . 8_565
O13 C12 N11 106.48(19) . .
O17 C12 O13 127.3(2) . .
O17 C12 N11 126.2(2) . .
C2 C1 C5 111.1(2) . .
C2 C1 C6 123.2(2) . .
C6 C1 C5 125.7(2) . .
H3A C3 H3B 109.4 . .
C2 C3 H3A 111.6 . .
C2 C3 H3B 111.6 . .
C2 C3 C4 101.1(2) . .
C4 C3 H3A 111.6 . .
C4 C3 H3B 111.6 . .
N11 C2 C3 124.6(2) . .
C1 C2 N11 123.1(2) . .
C1 C2 C3 112.3(2) . .
O10 C6 O7 122.5(2) . .
O10 C6 C1 125.0(2) . .
O7 C6 C1 112.4(2) . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16B 109.5 . .
C14 C16 H16C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
O13 C14 C16 101.56(19) . .
O13 C14 C15 109.72(13) . .
O13 C14 C15 109.72(13) . 8_565
C15 C14 C16 111.17(15) 8_565 .
C15 C14 C16 111.17(15) . .
C15 C14 C15 112.9(2) . 8_565
C19A C18 C19A 153.3(4) . 8_565
C19A C18 C4 124.1(3) . .
C19A C18 C4 81.8(2) 8_565 .
C19A C18 C4 124.1(3) 8_565 8_565
C19A C18 C4 81.8(2) . 8_565
C19B C18 C4 162.0(3) 8_565 8_565
C19B C18 C4 162.0(3) . .
C19B C18 C4 119.9(3) 8_565 .
C19B C18 C4 119.9(3) . 8_565
C19B C18 C19B 77.5(5) . 8_565
O7 C8 C9 104.5(3) . .
O7 C8 H8A 110(2) . .
O7 C8 H8B 107(3) . .
C9 C8 H8A 114.2(18) . .
C9 C8 H8B 112(3) . .
H8A C8 H8B 109(2) . .
C18 C19A H19A 117.9 . .
C18 C19A C4 53.0(2) . 8_565
C18 C19A C20A 124.2(4) . .
C4 C19A H19A 64.9 8_565 .
C20A C19A H19A 117.9 . .
C20A C19A C4 177.2(4) . 8_565
C5 C4 C3 101.8(2) . .
C5 C4 H4 110.8 . .
C3 C4 H4 110.8 . .
C18 C4 C5 111.5(2) . .
C18 C4 C3 110.7(3) . .
C18 C4 H4 110.8 . .
C19A C20A H20A 120.7 . .
C21 C20A C19A 118.5(5) . .
C21 C20A H20A 120.7 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C20A C21 C21 129.8(3) . 8_565
C20A C21 H21 115.1 . .
C21 C21 H21 115.1 8_565 .
C20B C20B H20B 124.8 8_565 .
C20B C20B C19B 110.3(2) 8_565 .
C19B C20B H20B 124.8 . .
C18 C19B C20B 120.7(4) . .
C18 C19B H19B 119.6 . .
C20B C19B H19B 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O13 C12 1.345(3) .
O13 C14 1.481(3) .
O17 C12 1.201(3) .
N11 C12 1.374(3) .
N11 C2 1.375(3) .
N11 H11 0.870(5) .
O10 C6 1.221(3) .
C5 H5B 0.9900 .
C5 H5A 0.9900 .
C5 C1 1.504(3) .
C5 C4 1.575(4) .
O7 C6 1.337(3) .
O7 C8 1.485(4) .
O7 C8 1.485(4) 8_565
C1 C2 1.351(3) .
C1 C6 1.440(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C3 C2 1.497(3) .
C3 C4 1.594(4) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C16 C14 1.517(4) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C15 C14 1.506(3) .
C14 C15 1.506(3) 8_565
C18 C19A 1.371(4) .
C18 C19A 1.371(4) 8_565
C18 C4 1.545(4) 8_565
C18 C4 1.545(4) .
C18 C19B 1.395(3) .
C18 C19B 1.395(3) 8_565
C8 C9 1.499(5) .
C8 H8A 0.97(3) .
C8 H8B 0.9900(11) .
C19A H19A 0.9500 .
C19A C4 1.914(5) 8_565
C19A C20A 1.374(4) .
C4 H4 1.0000 .
C20A H20A 0.9500 .
C20A C21 1.352(4) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C21 C21 1.928(9) 8_565
C21 H21 0.9500 .
C20B C20B 0.773(8) 8_565
C20B H20B 0.9500 .
C20B C19B 1.401(3) .
C19B H19B 0.9500 .
