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_1520704
_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 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                110.000(3)
_cell_angle_beta                 95.830(3)
_cell_angle_gamma                100.677(3)
_cell_formula_units_Z            4
_cell_length_a                   11.7148(5)
_cell_length_b                   11.8534(5)
_cell_length_c                   14.1205(6)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    105
_cell_measurement_theta_max      54.931
_cell_measurement_theta_min      2.946
_cell_volume                     1781.51(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      105
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            53558
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.037
_diffrn_reflns_theta_min         2.945
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1347 before and 0.0753 after correction.
The Ratio of minimum to maximum transmission is 0.8195.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         6798
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.0847
_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^)+(0.1344P)^2^+1.5541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2272
_refine_ls_wR_factor_ref         0.2672
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3882
_reflns_number_total             6798
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01679_si_003.cif
_cod_data_source_block           lube95
_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_original_cell_volume        1781.51(13)
_cod_database_code               1520704
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.904
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
2. Restrained distances
 C46-C47A \\sim C46-C47B
 with sigma of 0.02
 C49A-C50 \\sim C49B-C50
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 0.8A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C49A) = Uanis(C49B)
Uanis(C47A) = Uanis(C47B)
4. Same fragment restrains
{C47A, O47A, O48A, C49A} sigma for 1-2: 0.02, 1-3: 0.04
as
{C47B, O47B, O48B, C49B}
5. Others
 Sof(H46c)=Sof(H46d)=Sof(C47B)=Sof(O47B)=Sof(O48B)=Sof(C49B)=Sof(H49c)=
 Sof(H49d)=1-FVAR(1)
 Sof(H46a)=Sof(H46b)=Sof(C47A)=Sof(O47A)=Sof(O48A)=Sof(C49A)=Sof(H49a)=
 Sof(H49b)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C3(H3), C33(H33)
6.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C16(H16a,H16b), C19(H19a,H19b), C45(H45a,H45b), C46(H46a,
 H46b), C46(H46c,H46d), C49A(H49a,H49b), C49B(H49c,H49d)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), N31(H31), C37(H37), C38(H38),
  C39(H39), C40(H40), C42(H42), C43(H43), C44(H44), C51(H51), C52(H52),
 C53(H53), C54(H54), C55(H55)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'