#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/18/8101853.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_8101853
loop_
_publ_author_name
'Zonouzi, A.'
'Rahmani, H.'
'Samareh Afsari, H.'
'Nezamabadi, M.'
_publ_section_title
;
Crystal structure of dimethyl 2-(tert-butylamino)-7,7-dimethyl-5-oxo-
5,6,7,8-tetrahydro-4H-chromene-3,4-dicarboxylate, C₁₉H₂₇NO₆
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              545
_journal_page_last               546
_journal_volume                  220
_journal_year                    2005
_chemical_formula_sum            'C19 H27 N O6'
_chemical_formula_weight         365.42
_chemical_name_systematic
; 
dimethyl 2-(tert-butylamino)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-
chromene-3,4-dicarboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 90.32(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.457(3)
_cell_length_b                   8.978(2)
_cell_length_c                   15.790(4)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      10
_cell_volume                     1907.7(8)
_computing_cell_refinement       'Siemens P3/PC (Siemens, 1989)'
_computing_data_collection       'Siemens P3/PC (Siemens, 1989)'
_computing_data_reduction        'Siemens P3/PC (Siemens, 1989)'
_computing_molecular_graphics    'SHELXTL PLUS 5 (Sheldrick, 1998)'
_computing_publication_material  'SHELXTL PLUS 5 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL PLUS 5 (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL PLUS 5 (Sheldrick, 1998)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rebuild Syntex P2₁/Siemens P3'
_diffrn_measurement_method       theta/2theta
_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  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4410
_diffrn_reflns_theta_full        27.06
_diffrn_reflns_theta_max         27.06
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0431
_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)+(0.0500P)²+0.6694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                3240
_reflns_number_total             4142
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            1267-1632.cff
_cod_data_source_block           zo5
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1907.7(9)
_cod_original_sg_symbol_H-M      P12(1)/c1
_cod_database_code               8101853
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.85922(10) 0.08627(14) 0.74588(8) 0.0325(3) Uani 1 4 e d . . .
H1N H 0.8923 0.1089 0.6980 0.039 Uiso 1 4 e d R . .
O1 O 0.51002(9) -0.36146(15) 0.67228(7) 0.0479(3) Uani 1 4 e d . . .
O2 O 0.88441(9) 0.04937(12) 0.57705(7) 0.0380(3) Uani 1 4 e d . . .
O3 O 0.80986(8) -0.15318(12) 0.52109(6) 0.0357(3) Uani 1 4 e d . . .
O4 O 0.73635(9) -0.45929(12) 0.59458(7) 0.0380(3) Uani 1 4 e d . . .
O5 O 0.80802(10) -0.41154(14) 0.71923(8) 0.0476(3) Uani 1 4 e d . . .
O6 O 0.75001(8) -0.06515(11) 0.80922(6) 0.0294(2) Uani 1 4 e d . . .
C1 C 0.79472(10) -0.02450(16) 0.73491(9) 0.0270(3) Uani 1 4 e d . . .
C2 C 0.77286(11) -0.09571(16) 0.65993(9) 0.0275(3) Uani 1 4 e d . . .
C3 C 0.70057(11) -0.22460(16) 0.65835(9) 0.0267(3) Uani 1 4 e d . . .
H3A H 0.6602 -0.2196 0.6066 0.032 Uiso 1 4 e calc R . .
C4 C 0.63376(10) -0.21481(16) 0.73456(9) 0.0258(3) Uani 1 4 e d . . .
C5 C 0.53636(11) -0.28747(17) 0.73318(9) 0.0301(3) Uani 1 4 e d . . .
C6 C 0.47073(11) -0.26269(18) 0.80881(9) 0.0323(3) Uani 1 4 e d . . .
H6A H 0.4201 -0.3395 0.8102 0.039 Uiso 1 4 e calc R . .
H6B H 0.4375 -0.1673 0.8030 0.039 Uiso 1 4 e calc R . .
C7 C 0.52944(11) -0.26522(16) 0.89256(9) 0.0286(3) Uani 1 4 e d . . .
C8 C 0.61136(11) -0.14657(16) 0.88823(8) 0.0272(3) Uani 1 4 e d . . .
H8A H 0.5822 -0.0492 0.8978 0.033 Uiso 1 4 e calc R . .
H8B H 0.6594 -0.1647 0.9331 0.033 Uiso 1 4 e calc R . .
C9 C 0.66343(10) -0.14620(15) 0.80530(9) 0.0255(3) Uani 1 4 e d . . .
C10 C 0.45990(12) -0.2281(2) 0.96563(10) 0.0382(4) Uani 1 4 e d . . .
H10A H 0.4965 -0.2297 1.0180 0.057 Uiso 1 4 e calc R . .
H10B H 0.4074 -0.3004 0.9678 0.057 Uiso 1 4 e calc R . .
H10C H 0.4320 -0.1308 0.9571 0.057 Uiso 1 4 e calc R . .
C11 C 0.57472(13) -0.42015(18) 0.90553(11) 0.0375(4) Uani 1 4 e d . . .
H11A H 0.6116 -0.4219 0.9577 0.056 Uiso 1 4 e calc R . .
H11B H 0.6183 -0.4426 0.8593 0.056 Uiso 1 4 e calc R . .
H11C H 0.5226 -0.4930 0.9076 0.056 Uiso 1 4 e calc R . .
C12 C 0.82728(11) -0.05586(16) 0.58483(9) 0.0292(3) Uani 1 4 e d . . .
C13 C 0.86733(14) -0.1343(2) 0.44517(10) 0.0414(4) Uani 1 4 e d . . .
H13A H 0.8488 -0.2092 0.4047 0.062 Uiso 1 4 e calc R . .
H13B H 0.9367 -0.1436 0.4585 0.062 Uiso 1 4 e calc R . .
H13C H 0.8547 -0.0374 0.4217 0.062 Uiso 1 4 e calc R . .
C14 C 0.75475(11) -0.37414(17) 0.66190(9) 0.0292(3) Uani 1 4 e d . . .
C15 C 0.78442(14) -0.60327(19) 0.59514(12) 0.0438(4) Uani 1 4 e d . . .
H15A H 0.7669 -0.6566 0.5445 0.066 Uiso 1 4 e calc R . .
H15B H 0.7631 -0.6588 0.6437 0.066 Uiso 1 4 e calc R . .
H15C H 0.8552 -0.5900 0.5976 0.066 Uiso 1 4 e calc R . .
C16 C 0.88190(11) 0.17209(17) 0.82365(10) 0.0323(3) Uani 1 4 e d . . .
C17 C 0.92769(14) 0.0717(2) 0.89144(12) 0.0457(4) Uani 1 4 e d . . .
H17A H 0.8799 -0.0016 0.9086 0.069 Uiso 1 4 e calc R . .
H17B H 0.9468 0.1308 0.9395 0.069 Uiso 1 4 e calc R . .
H17C H 0.9852 0.0227 0.8689 0.069 Uiso 1 4 e calc R . .
C18 C 0.95852(13) 0.2883(2) 0.79653(12) 0.0448(4) Uani 1 4 e d . . .
H18A H 1.0168 0.2389 0.7759 0.067 Uiso 1 4 e calc R . .
H18B H 0.9760 0.3495 0.8442 0.067 Uiso 1 4 e calc R . .
H18C H 0.9308 0.3494 0.7525 0.067 Uiso 1 4 e calc R . .
C19 C 0.78900(13) 0.25056(19) 0.85653(12) 0.0411(4) Uani 1 4 e d . . .
H19A H 0.7409 0.1775 0.8733 0.062 Uiso 1 4 e calc R . .
H19B H 0.7614 0.3120 0.8126 0.062 Uiso 1 4 e calc R . .
H19C H 0.8064 0.3114 0.9043 0.062 Uiso 1 4 e 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C16 128.93(13) . . ?
C1 N1 H1N 112.5 . . ?
C16 N1 H1N 118.5 . . ?
C12 O3 C13 116.85(12) . . ?
C14 O4 C15 115.31(13) . . ?
C1 O6 C9 118.57(11) . . ?
N1 C1 O6 112.12(12) . . ?
N1 C1 C2 126.54(13) . . ?
O6 C1 C2 121.33(13) . . ?
C1 C2 C12 119.02(13) . . ?
C1 C2 C3 120.28(12) . . ?
C12 C2 C3 120.39(13) . . ?
C4 C3 C2 109.18(12) . . ?
C4 C3 C14 107.95(11) . . ?
C2 C3 C14 111.40(12) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C14 C3 H3A 109.4 . . ?
C9 C4 C5 118.80(13) . . ?
C9 C4 C3 121.17(13) . . ?
C5 C4 C3 119.97(12) . . ?
O1 C5 C4 120.70(14) . . ?
O1 C5 C6 122.45(14) . . ?
C4 C5 C6 116.83(13) . . ?
C5 C6 C7 112.29(12) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C10 C7 C11 110.03(13) . . ?
C10 C7 C8 109.00(13) . . ?
C11 C7 C8 110.54(12) . . ?
C10 C7 C6 109.44(13) . . ?
C11 C7 C6 109.30(13) . . ?
C8 C7 C6 108.50(11) . . ?
C9 C8 C7 112.48(12) . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C4 C9 O6 122.11(13) . . ?
C4 C9 C8 126.52(13) . . ?
O6 C9 C8 111.37(11) . . ?
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 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 O3 122.01(13) . . ?
O2 C12 C2 126.57(14) . . ?
O3 C12 C2 111.40(12) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O4 123.33(15) . . ?
O5 C14 C3 123.81(13) . . ?
O4 C14 C3 112.86(12) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 110.78(13) . . ?
N1 C16 C19 110.89(13) . . ?
C17 C16 C19 111.20(14) . . ?
N1 C16 C18 105.01(13) . . ?
C17 C16 C18 109.21(14) . . ?
C19 C16 C18 109.55(13) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3307(19) . ?
N1 C16 1.4800(19) . ?
N1 H1N 0.9029 . ?
O1 C5 1.2197(18) . ?
O2 C12 1.2246(18) . ?
O3 C12 1.3522(18) . ?
O3 C13 1.4403(18) . ?
O4 C14 1.3314(17) . ?
O4 C15 1.445(2) . ?
O5 C14 1.1995(19) . ?
O6 C1 1.3711(17) . ?
O6 C9 1.3747(17) . ?
C1 C2 1.376(2) . ?
C2 C12 1.442(2) . ?
C2 C3 1.512(2) . ?
C3 C4 1.5087(19) . ?
C3 C14 1.529(2) . ?
C3 H3A 0.9800 . ?
C4 C9 1.335(2) . ?
C4 C5 1.464(2) . ?
C5 C6 1.506(2) . ?
C6 C7 1.537(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C10 1.527(2) . ?
C7 C11 1.532(2) . ?
C7 C8 1.535(2) . ?
C8 C9 1.4887(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.527(2) . ?
C16 C19 1.528(2) . ?
C16 C18 1.530(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N1 C1 O6 -4.2(2) . . . . ?
C16 N1 C1 C2 176.46(15) . . . . ?
C9 O6 C1 N1 161.91(12) . . . . ?
C9 O6 C1 C2 -18.7(2) . . . . ?
N1 C1 C2 C12 3.7(2) . . . . ?
O6 C1 C2 C12 -175.53(13) . . . . ?
N1 C1 C2 C3 177.44(14) . . . . ?
O6 C1 C2 C3 -1.8(2) . . . . ?
C1 C2 C3 C4 22.48(18) . . . . ?
C12 C2 C3 C4 -163.89(13) . . . . ?
C1 C2 C3 C14 -96.64(16) . . . . ?
C12 C2 C3 C14 76.99(16) . . . . ?
C2 C3 C4 C9 -25.97(18) . . . . ?
C14 C3 C4 C9 95.27(16) . . . . ?
C2 C3 C4 C5 156.98(13) . . . . ?
C14 C3 C4 C5 -81.77(16) . . . . ?
C9 C4 C5 O1 -174.01(15) . . . . ?
C3 C4 C5 O1 3.1(2) . . . . ?
C9 C4 C5 C6 7.5(2) . . . . ?
C3 C4 C5 C6 -175.34(13) . . . . ?
O1 C5 C6 C7 141.68(16) . . . . ?
C4 C5 C6 C7 -39.92(18) . . . . ?
C5 C6 C7 C10 175.83(13) . . . . ?
C5 C6 C7 C11 -63.61(16) . . . . ?
C5 C6 C7 C8 57.01(16) . . . . ?
C10 C7 C8 C9 -162.55(12) . . . . ?
C11 C7 C8 C9 76.40(15) . . . . ?
C6 C7 C8 C9 -43.45(16) . . . . ?
C5 C4 C9 O6 -174.48(12) . . . . ?
C3 C4 C9 O6 8.4(2) . . . . ?
C5 C4 C9 C8 6.2(2) . . . . ?
C3 C4 C9 C8 -170.92(13) . . . . ?
C1 O6 C9 C4 15.5(2) . . . . ?
C1 O6 C9 C8 -165.03(12) . . . . ?
C7 C8 C9 C4 13.5(2) . . . . ?
C7 C8 C9 O6 -165.97(11) . . . . ?
C13 O3 C12 O2 4.5(2) . . . . ?
C13 O3 C12 C2 -174.08(13) . . . . ?
C1 C2 C12 O2 -9.6(2) . . . . ?
C3 C2 C12 O2 176.69(14) . . . . ?
C1 C2 C12 O3 168.92(13) . . . . ?
C3 C2 C12 O3 -4.79(19) . . . . ?
C15 O4 C14 O5 0.7(2) . . . . ?
C15 O4 C14 C3 -179.04(13) . . . . ?
C4 C3 C14 O5 -59.53(19) . . . . ?
C2 C3 C14 O5 60.32(19) . . . . ?
C4 C3 C14 O4 120.24(13) . . . . ?
C2 C3 C14 O4 -119.90(13) . . . . ?
C1 N1 C16 C17 64.5(2) . . . . ?
C1 N1 C16 C19 -59.4(2) . . . . ?
C1 N1 C16 C18 -177.68(15) . . . . ?
