#------------------------------------------------------------------------------
#$Date: 2019-11-25 08:23:26 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240500 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/98/4129848.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_4129848
loop_
_publ_author_name
'Tallmadge, Evan H.'
'Jermaks, Janis'
'Collum, David B.'
_publ_section_title
;
 Structure-Reactivity Relationships in Lithiated Evans Enolates: Influence
 of Aggregation and Solvation on the Stereochemistry and Mechanism of
 Aldol Additions.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              345
_journal_page_last               355
_journal_paper_doi               10.1021/jacs.5b10980
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H25 N O4'
_chemical_formula_sum            'C19 H25 N O4'
_chemical_formula_weight         331.40
_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   difmap
_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                   5.7701(6)
_cell_length_b                   13.3976(12)
_cell_length_c                   22.752(2)
_cell_measurement_reflns_used    1507
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.80
_cell_measurement_theta_min      3.04
_cell_volume                     1758.9(3)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT+'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5883
_diffrn_reflns_theta_full        23.84
_diffrn_reflns_theta_max         23.84
_diffrn_reflns_theta_min         1.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.9495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0356
_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)+(0.0341P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0808
_reflns_number_gt                1732
_reflns_number_total             2552
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b10980_si_001.cif
_cod_data_source_block           et2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1758.8(3)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4129848
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
O1 O 0.4296(3) 0.69296(13) -0.00121(8) 0.0676(6) Uani 1 1 d .
O2 O 0.4965(4) 0.75415(15) 0.08819(9) 0.0773(6) Uani 1 1 d .
O3 O 0.9589(3) 0.51577(14) 0.09110(8) 0.0662(6) Uani 1 1 d .
O4 O 0.9808(3) 0.48344(12) 0.21081(7) 0.0624(5) Uani 1 1 d .
H4A H 1.0331 0.4771 0.1775 0.094 Uiso 1 1 calc R
N1 N 0.6643(4) 0.60551(14) 0.05630(8) 0.0443(6) Uani 1 1 d .
C1 C 0.5273(5) 0.6904(2) 0.05222(12) 0.0555(7) Uani 1 1 d .
C2 C 0.5259(6) 0.61623(19) -0.03833(11) 0.0658(9) Uani 1 1 d .
H2A H 0.6360 0.6445 -0.0659 0.079 Uiso 1 1 calc R
H2B H 0.4045 0.5827 -0.0602 0.079 Uiso 1 1 calc R
C3 C 0.6456(5) 0.54408(18) 0.00307(10) 0.0471(7) Uani 1 1 d .
H3A H 0.8001 0.5271 -0.0118 0.057 Uiso 1 1 calc R
C4 C 0.8138(5) 0.57966(19) 0.10146(11) 0.0473(7) Uani 1 1 d .
C5 C 0.7865(4) 0.62443(17) 0.16208(11) 0.0467(7) Uani 1 1 d .
H5A H 0.6414 0.6624 0.1628 0.056 Uiso 1 1 calc R
C6 C 0.7690(4) 0.53974(18) 0.20852(10) 0.0441(7) Uani 1 1 d .
C7 C 0.5682(4) 0.47007(18) 0.19410(10) 0.0500(7) Uani 1 1 d .
H7A H 0.4286 0.5094 0.1890 0.060 Uiso 1 1 calc R
H7B H 0.6002 0.4367 0.1572 0.060 Uiso 1 1 calc R
C8 C 0.5253(6) 0.3916(2) 0.24141(11) 0.0652(8) Uani 1 1 d .
H8A H 0.3891 0.3529 0.2312 0.078 Uiso 1 1 calc R
H8B H 0.6565 0.3464 0.2430 0.078 Uiso 1 1 calc R
C9 C 0.4904(6) 0.4384(2) 0.30102(12) 0.0751(9) Uani 1 1 d .
H9A H 0.4735 0.3866 0.3305 0.090 Uiso 1 1 calc R
H9B H 0.3502 0.4783 0.3009 0.090 Uiso 1 1 calc R
C10 C 0.6968(6) 0.5037(2) 0.31590(11) 0.0724(9) Uani 1 1 d .
H10A H 0.8343 0.4624 0.3191 0.087 Uiso 1 1 calc R
H10B H 0.6711 0.5354 0.3537 0.087 Uiso 1 1 calc R
C11 C 0.7367(6) 0.5836(2) 0.26949(11) 0.0637(8) Uani 1 1 d .
H11A H 0.8731 0.6220 0.2798 0.076 Uiso 1 1 calc R
H11B H 0.6052 0.6287 0.2690 0.076 Uiso 1 1 calc R
C12 C 0.9875(6) 0.69756(19) 0.17253(13) 0.0789(10) Uani 1 1 d .
H12A H 0.9877 0.7474 0.1422 0.118 Uiso 1 1 calc R
H12B H 1.1316 0.6618 0.1718 0.118 Uiso 1 1 calc R
H12C H 0.9685 0.7292 0.2101 0.118 Uiso 1 1 calc R
C13 C 0.5087(5) 0.44956(17) 0.01664(10) 0.0545(7) Uani 1 1 d .
H13A H 0.5832 0.4147 0.0489 0.065 Uiso 1 1 calc R
H13B H 0.3542 0.4681 0.0294 0.065 Uiso 1 1 calc R
C14 C 0.4892(5) 0.38007(17) -0.03478(10) 0.0447(7) Uani 1 1 d .
C15 C 0.2988(5) 0.3791(2) -0.07138(13) 0.0624(8) Uani 1 1 d .
H15A H 0.1773 0.4233 -0.0645 0.075 Uiso 1 1 calc R
C16 C 0.2856(6) 0.3138(2) -0.11812(13) 0.0708(9) Uani 1 1 d .
H16A H 0.1561 0.3146 -0.1425 0.085 Uiso 1 1 calc R
C17 C 0.4593(6) 0.2484(2) -0.12891(12) 0.0652(8) Uani 1 1 d .
H17A H 0.4491 0.2045 -0.1605 0.078 Uiso 1 1 calc R
C18 C 0.6497(6) 0.2472(2) -0.09318(13) 0.0660(8) Uani 1 1 d .
H18A H 0.7691 0.2022 -0.1003 0.079 Uiso 1 1 calc R
C19 C 0.6653(5) 0.31319(19) -0.04616(12) 0.0555(8) Uani 1 1 d .
H19A H 0.7957 0.3122 -0.0221 0.067 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C2 110.5(2)
C4 N1 C1 127.5(2)
C4 N1 C3 121.1(2)
C1 N1 C3 111.3(2)
O2 C1 O1 122.7(3)
O2 C1 N1 128.6(3)
O1 C1 N1 108.7(2)
O1 C2 C3 105.45(19)
N1 C3 C2 100.86(19)
N1 C3 C13 109.66(18)
C2 C3 C13 114.8(2)
O3 C4 N1 117.3(2)
O3 C4 C5 121.7(3)
N1 C4 C5 120.8(2)
C4 C5 C12 108.4(2)
C4 C5 C6 109.72(19)
C12 C5 C6 114.2(2)
O4 C6 C11 105.9(2)
O4 C6 C7 109.45(18)
C11 C6 C7 109.9(2)
O4 C6 C5 110.6(2)
C11 C6 C5 110.3(2)
C7 C6 C5 110.52(19)
C8 C7 C6 113.2(2)
C9 C8 C7 111.7(2)
C8 C9 C10 109.6(2)
C9 C10 C11 111.7(2)
C10 C11 C6 112.4(2)
C14 C13 C3 113.37(19)
C15 C14 C19 117.9(2)
C15 C14 C13 122.5(3)
C19 C14 C13 119.6(3)
C14 C15 C16 121.0(3)
C17 C16 C15 120.6(3)
C16 C17 C18 119.7(3)
C17 C18 C19 120.1(3)
C14 C19 C18 120.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.340(3)
O1 C2 1.442(3)
O2 C1 1.196(3)
O3 C4 1.220(3)
O4 C6 1.437(3)
N1 C4 1.386(3)
N1 C1 1.388(3)
N1 C3 1.468(3)
C2 C3 1.516(3)
C3 C13 1.524(3)
C4 C5 1.512(3)
C5 C12 1.537(3)
C5 C6 1.554(3)
C6 C11 1.518(3)
C6 C7 1.523(3)
C7 C8 1.525(3)
C8 C9 1.508(3)
C9 C10 1.516(4)
C10 C11 1.521(3)
C13 C14 1.499(3)
C14 C15 1.379(4)
C14 C19 1.379(3)
C15 C16 1.380(4)
C16 C17 1.353(4)
C17 C18 1.367(4)
C18 C19 1.391(4)
