data_16srv107
_audit_creation_date              2016-03-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         'Batsanov, Andrei S.'
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         
'4-tert-butyl 2-ethyl 5-(4-bromo-3-iodophenyl)-1-ethyl-4-methylpyrrolidine-2,4-dicarboxylate'
_chemical_formula_moiety          'C24 H33 Br I N O5'
_chemical_formula_sum             'C24 H33 Br I N O5'
_chemical_formula_weight          622.32
_chemical_melting_point           ?
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'
 'Br' 'Br' -0.2901 2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system       'triclinic'
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                    8.8223(5)
_cell_length_b                    9.7894(5)
_cell_length_c                    17.1881(9)
_cell_angle_alpha                 94.4785(19)
_cell_angle_beta                  101.2553(19)
_cell_angle_gamma                 116.2515(17)
_cell_volume                      1282.73(12)
_cell_formula_units_Z             2
_cell_measurement_reflns_used     9982
_cell_measurement_temperature     120
_cell_measurement_theta_max       34.36
_cell_measurement_theta_min       2.36
_shelx_estimated_absorpt_T_max    0.742
_shelx_estimated_absorpt_T_min    0.588
_exptl_absorpt_coefficient_mu     2.839
_exptl_absorpt_correction_T_max   0.8041
_exptl_absorpt_correction_T_min   0.6748
_exptl_absorpt_correction_type    integration
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0739 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.6627.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.611
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        block
_exptl_crystal_F_000              624
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 0.00 0.00 1.00 0.0400
 0.00 0.00 -1.00 0.0560
 -2.00 1.00 -2.00 0.0620
 2.00 -1.00 -2.00 0.0990
 -2.00 1.00 2.00 0.0820
 0.00 -2.00 1.00 0.0770
 0.00 2.00 -1.00 0.0520
 0.00 -2.00 -1.00 0.0680
 -1.00 2.00 0.00 0.0550
 -1.00 1.00 -2.00 0.0460
 1.00 -1.00 2.00 0.0700
 0.00 1.00 -2.00 0.0490
 1.00 -2.00 2.00 0.0800
 -2.00 0.00 1.00 0.0870

_exptl_crystal_size_max           0.209
_exptl_crystal_size_mid           0.151
_exptl_crystal_size_min           0.112
_exptl_special_details
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of narrow-frame ω-scans (scan 
width 0.5°, 8s exposure), every run at a different φ angle.
Two runs of φ-scans (scan width 1°, 1s exposure) were used for 
scaling overflowing intensities. Crystal to detector distance 3.49 cm.
;
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0312
_diffrn_reflns_av_unetI/netI      0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_l_max        27
_diffrn_reflns_limit_l_min        -28
_diffrn_reflns_number             34192
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full         30.000
_diffrn_reflns_theta_max          35.849
_diffrn_reflns_theta_min          2.361
_diffrn_ambient_temperature       120
_diffrn_detector_area_resol_mean  ?
_diffrn_detector_type             'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device        '3-circle area detector diffractometer'
_diffrn_measurement_device_type   'Bruker D8 Venture'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_radiation_monochromator   'focusing mirrors'
_diffrn_radiation_probe           X-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'ImuS microsource'
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 9096
_reflns_number_total              10848
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing.bruker_data_scaling    'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement        'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection        'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction         'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution     'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max          1.893
_refine_diff_density_min          -0.543
_refine_diff_density_rms          0.106
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.032
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      305
_refine_ls_number_reflns          10848
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0398
_refine_ls_R_factor_gt            0.0274
_refine_ls_restrained_S_all       1.032
_refine_ls_shift/su_max           0.003
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0240P)²+0.5310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0557
_refine_ls_wR_factor_ref          0.0591
_refine_special_details
;
 Methyl groups were refined as rigid bodies rotating around C---C 
 bonds, with a common refined U for three H atoms. Other H atoms: 
 riding model.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Uiso(H8A)=Uiso(H8B)=Uiso(H8C)=FVAR(1)
 Uiso(H9A)=Uiso(H9B)=Uiso(H9C)=FVAR(2)
 Uiso(H10A)=Uiso(H10B)=Uiso(H10C)=FVAR(3)
 Uiso(H12A)=Uiso(H12B)=Uiso(H12C)=FVAR(4)
 Uiso(H13A)=Uiso(H13B)=Uiso(H13C)=FVAR(5)
 Uiso(H16A)=Uiso(H16B)=Uiso(H16C)=FVAR(6)
 Uiso(H17A)=Uiso(H17B)=Uiso(H17C)=FVAR(7)
 Uiso(H18A)=Uiso(H18B)=Uiso(H18C)=FVAR(8)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C23(H23), C24(H24)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    ?
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
 I I 0.55381(2) 0.64759(2) 0.34315(2) 0.01596(3) Uani 1 1 d . . . . .
 Br Br 0.77498(2) 0.60640(2) 0.52676(2) 0.02164(4) Uani 1 1 d . . . . .
 O1 O 0.29472(15) 0.21491(13) -0.01411(6) 0.0204(2) Uani 1 1 d . . . . .
 O2 O 0.41906(16) 0.37514(13) 0.10666(7) 0.0221(2) Uani 1 1 d . . . . .
 O3 O 0.23501(14) -0.02310(12) 0.28546(6) 0.01571(19) Uani 1 1 d . . . . .
 O4 O 0.42450(15) -0.11778(13) 0.32060(7) 0.0203(2) Uani 1 1 d . . . . .
 O5 O 0.69532(15) 0.29838(14) 0.04299(7) 0.0238(2) Uani 1 1 d . . . . .
 N N 0.60063(15) 0.19301(13) 0.14497(7) 0.0126(2) Uani 1 1 d . . . . .
 C1 C 0.38328(19) 0.25620(17) 0.06327(8) 0.0157(3) Uani 1 1 d . . . . .
 C2 C 0.42379(18) 0.12976(16) 0.09118(8) 0.0141(2) Uani 1 1 d . . . . .
 H2 H 0.4102 0.0564 0.0433 0.017 Uiso 1 1 calc R . . . .
 C3 C 0.30571(18) 0.04101(17) 0.14346(9) 0.0158(3) Uani 1 1 d . . . . .
 H3A H 0.1966 -0.0479 0.1099 0.019 Uiso 1 1 calc R . . . .
 H3B H 0.2754 0.1095 0.1753 0.019 Uiso 1 1 calc R . . . .
 C4 C 0.41719(18) -0.01438(16) 0.19868(8) 0.0135(2) Uani 1 1 d . . . . .
 C5 C 0.60177(18) 0.13149(15) 0.22055(8) 0.0127(2) Uani 1 1 d . . . . .
 H5 H 0.6934 0.0964 0.2298 0.015 Uiso 1 1 calc R . . . .
 C6 C 0.73492(19) 0.27149(16) 0.11056(9) 0.0155(3) Uani 1 1 d . . . . .
 C7 C 0.92647(19) 0.31636(17) 0.15026(9) 0.0170(3) Uani 1 1 d . . . . .
 C8 C 0.9895(2) 0.3780(2) 0.24163(10) 0.0263(3) Uani 1 1 d . . . . .
 H8A H 0.9471 0.4517 0.2550 0.033(3) Uiso 1 1 calc GR . . . .
 H8B H 1.1177 0.4303 0.2581 0.033(3) Uiso 1 1 calc GR . . . .
 H8C H 0.9442 0.2914 0.2701 0.033(3) Uiso 1 1 calc GR . . . .
 C9 C 1.0409(2) 0.4434(2) 0.10950(13) 0.0295(4) Uani 1 1 d . . . . .
 H9A H 1.0011 0.4083 0.0508 0.034(3) Uiso 1 1 calc GR . . . .
 H9B H 1.1630 0.4650 0.1282 0.034(3) Uiso 1 1 calc GR . . . .
 H9C H 1.0318 0.5380 0.1235 0.034(3) Uiso 1 1 calc GR . . . .
 C10 C 0.9493(2) 0.1718(2) 0.13078(12) 0.0289(4) Uani 1 1 d . . . . .
 H10A H 0.8748 0.0888 0.1554 0.037(4) Uiso 1 1 calc GR . . . .
 H10B H 1.0719 0.1970 0.1524 0.037(4) Uiso 1 1 calc GR . . . .
 H10C H 0.9160 0.1373 0.0721 0.037(4) Uiso 1 1 calc GR . . . .
 C11 C 0.2447(2) 0.3271(2) -0.04670(10) 0.0249(3) Uani 1 1 d . . . . .
 H11A H 0.3415 0.4337 -0.0261 0.030 Uiso 1 1 calc R . . . .
 H11B H 0.1406 0.3200 -0.0301 0.030 Uiso 1 1 calc R . . . .
 C12 C 0.2050(3) 0.2898(2) -0.13642(10) 0.0279(4) Uani 1 1 d . . . . .
 H12A H 0.1769 0.3666 -0.1598 0.041(4) Uiso 1 1 calc GR . . . .
 H12B H 0.1049 0.1863 -0.1564 0.041(4) Uiso 1 1 calc GR . . . .
 H12C H 0.3071 0.2922 -0.1521 0.041(4) Uiso 1 1 calc GR . . . .
 C13 C 0.4278(2) -0.15013(17) 0.15350(9) 0.0200(3) Uani 1 1 d . . . . .
 H13A H 0.4843 -0.1164 0.1098 0.031(3) Uiso 1 1 calc GR . . . .
 H13B H 0.3095 -0.2359 0.1307 0.031(3) Uiso 1 1 calc GR . . . .
 H13C H 0.4962 -0.1848 0.1911 0.031(3) Uiso 1 1 calc GR . . . .
 C14 C 0.36035(19) -0.05850(16) 0.27525(9) 0.0146(2) Uani 1 1 d . . . . .
 C15 C 0.1659(2) -0.04887(18) 0.35827(9) 0.0171(3) Uani 1 1 d . . . . .
 C16 C 0.3122(2) 0.0439(2) 0.43390(10) 0.0256(3) Uani 1 1 d . . . . .
 H16A H 0.3939 0.0004 0.4421 0.036(3) Uiso 1 1 calc GR . . . .
 H16B H 0.2628 0.0390 0.4806 0.036(3) Uiso 1 1 calc GR . . . .
 H16C H 0.3744 0.1521 0.4278 0.036(3) Uiso 1 1 calc GR . . . .
 C17 C 0.0744(2) -0.22160(19) 0.35946(10) 0.0236(3) Uani 1 1 d . . . . .
 H17A H -0.0141 -0.2767 0.3082 0.032(3) Uiso 1 1 calc GR . . . .
 H17B H 0.0179 -0.2390 0.4041 0.032(3) Uiso 1 1 calc GR . . . .
 H17C H 0.1604 -0.2603 0.3668 0.032(3) Uiso 1 1 calc GR . . . .
 C18 C 0.0351(2) 0.0140(2) 0.34420(10) 0.0219(3) Uani 1 1 d . . . . .
 H18A H 0.0941 0.1216 0.3366 0.025(3) Uiso 1 1 calc GR . . . .
 H18B H -0.0137 0.0099 0.3910 0.025(3) Uiso 1 1 calc GR . . . .
 H18C H -0.0593 -0.0491 0.2959 0.025(3) Uiso 1 1 calc GR . . . .
 C19 C 0.63636(18) 0.24752(16) 0.29442(8) 0.0128(2) Uani 1 1 d . . . . .
 C20 C 0.59060(18) 0.36623(16) 0.28881(8) 0.0131(2) Uani 1 1 d . . . . .
 H20 H 0.5339 0.3746 0.2378 0.016 Uiso 1 1 calc R . . . .
 C21 C 0.62740(18) 0.47333(16) 0.35761(8) 0.0135(2) Uani 1 1 d . . . . .
 C22 C 0.71182(19) 0.46118(17) 0.43199(8) 0.0151(2) Uani 1 1 d . . . . .
 C23 C 0.7572(2) 0.34262(17) 0.43815(9) 0.0177(3) Uani 1 1 d . . . . .
 H23 H 0.8147 0.3347 0.4891 0.021 Uiso 1 1 calc R . . . .
 C24 C 0.71867(19) 0.23611(17) 0.36990(9) 0.0167(3) Uani 1 1 d . . . . .
 H24 H 0.7485 0.1545 0.3745 0.020 Uiso 1 1 calc R . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
 I C21 2.0921(14) . ?
 Br C22 1.8890(14) . ?
 O1 C1 1.3319(17) . ?
 O1 C11 1.4633(18) . ?
 O2 C1 1.2077(18) . ?
 O3 C14 1.3338(17) . ?
 O3 C15 1.4873(17) . ?
 O4 C14 1.2057(17) . ?
 O5 C6 1.2293(18) . ?
 N C2 1.4715(17) . ?
 N C5 1.4741(17) . ?
 N C6 1.3722(18) . ?
 C1 C2 1.5189(19) . ?
 C2 C3 1.528(2) . ?
 C3 C4 1.5330(19) . ?
 C4 C5 1.5660(19) . ?
 C4 C13 1.534(2) . ?
 C4 C14 1.5247(19) . ?
 C5 C19 1.5207(19) . ?
 C6 C7 1.536(2) . ?
 C7 C8 1.534(2) . ?
 C7 C9 1.536(2) . ?
 C7 C10 1.537(2) . ?
 C11 C12 1.491(2) . ?
 C15 C16 1.518(2) . ?
 C15 C17 1.522(2) . ?
 C15 C18 1.520(2) . ?
 C19 C20 1.3930(18) . ?
 C19 C24 1.3962(19) . ?
 C20 C21 1.3995(19) . ?
 C21 C22 1.3905(19) . ?
 C22 C23 1.390(2) . ?
 C23 C24 1.385(2) . ?

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 O1 C11 115.62(12) . . ?
 C14 O3 C15 121.50(11) . . ?
 C2 N C5 112.79(11) . . ?
 C6 N C2 115.27(11) . . ?
 C6 N C5 130.43(12) . . ?
 O1 C1 C2 111.10(12) . . ?
 O2 C1 O1 124.46(13) . . ?
 O2 C1 C2 124.35(13) . . ?
 N C2 C1 112.26(11) . . ?
 N C2 C3 103.21(11) . . ?
 C1 C2 C3 111.62(12) . . ?
 C2 C3 C4 103.60(11) . . ?
 C3 C4 C5 101.77(10) . . ?
 C3 C4 C13 111.79(12) . . ?
 C13 C4 C5 108.79(11) . . ?
 C14 C4 C3 114.95(12) . . ?
 C14 C4 C5 110.25(11) . . ?
 C14 C4 C13 108.99(11) . . ?
 N C5 C4 101.71(10) . . ?
 N C5 C19 113.93(11) . . ?
 C19 C5 C4 114.42(11) . . ?
 O5 C6 N 117.01(13) . . ?
 O5 C6 C7 119.87(13) . . ?
 N C6 C7 123.00(12) . . ?
 C6 C7 C10 106.74(13) . . ?
 C8 C7 C6 116.17(12) . . ?
 C8 C7 C9 107.70(14) . . ?
 C8 C7 C10 110.07(14) . . ?
 C9 C7 C6 107.34(12) . . ?
 C9 C7 C10 108.58(14) . . ?
 O1 C11 C12 107.68(13) . . ?
 O3 C14 C4 112.33(12) . . ?
 O4 C14 O3 125.12(13) . . ?
 O4 C14 C4 122.55(13) . . ?
 O3 C15 C16 110.11(12) . . ?
 O3 C15 C17 109.72(12) . . ?
 O3 C15 C18 102.01(11) . . ?
 C16 C15 C17 112.70(13) . . ?
 C16 C15 C18 110.94(13) . . ?
 C18 C15 C17 110.84(13) . . ?
 C20 C19 C5 121.90(12) . . ?
 C20 C19 C24 119.04(13) . . ?
 C24 C19 C5 119.05(12) . . ?
 C19 C20 C21 120.63(12) . . ?
 C20 C21 I 117.86(10) . . ?
 C22 C21 I 122.78(10) . . ?
 C22 C21 C20 119.36(13) . . ?
 C21 C22 Br 121.87(11) . . ?
 C23 C22 Br 117.76(10) . . ?
 C23 C22 C21 120.35(13) . . ?
 C24 C23 C22 119.94(13) . . ?
 C23 C24 C19 120.67(13) . . ?

_shelx_SHELXL_version_number      '2014/7'
