γ-Turn Mimicry with Benzodiazepinones and Pyrrolobenzodiazepinones Synthesized from a Common Amino Ketone Intermediate.
Dörr, Aurélie A; Lubell, William D.; Organic letters 17 (2015) 3592–3595; doi:10.1021/acs.orglett.5b01679

data_1520705
_publ_section_title
;
 \g-Turn Mimicry with Benzodiazepinones and Pyrrolobenzodiazepinones
 Synthesized from a Common Amino Ketone Intermediate.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3592
_journal_page_last               3595
_journal_paper_doi               10.1021/acs.orglett.5b01679
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C22 H22 N2 O3'
_chemical_formula_sum            'C22 H22 N2 O3'
_chemical_formula_weight         362.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2013-08-16
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.6510(3)
_cell_length_b                   15.5231(3)
_cell_length_c                   13.7865(3)
_cell_measurement_reflns_used    9662
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.541
_cell_measurement_theta_min      2.846
_cell_volume                     3777.48(13)
_computing_cell_refinement
;
SAINT (2013) V8.30C; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.30C; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            73860
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.718
_diffrn_reflns_theta_min         2.847
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0728 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.9209.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       FRAGMENT
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 3266 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         7200
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0342
_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/[\s^2^(Fo^2^)+(0.0582P)^2^+0.9289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                7107
_reflns_number_total             7200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01679_si_005.cif
_cod_data_source_block           lube65
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1520704--1520706.cif.
;
_cod_database_code               1520705
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H22A,H22B} of C22, {H42A,H42B} of C42, {H21A,H21B} of C21,
   {H12A,H12B} of C12, {H14A,H14B} of C14, {H54A,H54B} of C54A, {H54C,H54D} of
  C54B, {H51A,H51B} of C51, {H44A,H44B} of C44, All C(H,H,H,H) groups
 At 1.5 times of:
  {H24A,H24B} of C24
2. Restrained distances
 C52-C53A \\sim C52-C53B
 with sigma of 0.01
 C52-C54A \\sim C52-C54B
 with sigma of 0.02
 C53A-C54A \\sim C53B-C54B
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C53A) = Uanis(C53B)
Uanis(C54A) = Uanis(C54B)
4. Others
 Sof(H52C)=Sof(H52D)=Sof(C53B)=Sof(H53B)=Sof(C54B)=Sof(H54C)=Sof(H54D)=1-FVAR(1)
 Sof(H52A)=Sof(H52B)=Sof(C53A)=Sof(H53A)=Sof(C54A)=Sof(H54A)=Sof(H54B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C33(H33)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C21(H21A,H21B), C22(H22A,H22B), C42(H42A,
 H42B), C44(H44A,H44B), C51(H51A,H51B), C52(H52A,H52B), C52(H52C,H52D)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C23(H23), C38(H38), C39(H39), C40(H40), C41(H41), C46(H46), C47(H47),
  C48(H48), C49(H49), C50(H50), C53A(H53A), C53B(H53B)
5.d X=CH2 refined with riding coordinates:
 C24(H24A,H24B), C54A(H54A,H54B), C54B(H54C,H54D)
;
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.886
_shelxl_version_number           2013-3