Asymmetric synthesis of chromene skeletons via organocatalytic domino reactions of in situ generated ortho-quinone methide with malononitrile and β-functionalized ketone
Zhang, Lili; Zhou, Xiao; Li, Pengfei; Liu, Zhantao; Liu, Yang; Sun, Yong; Li, Wenjun; RSC Adv. 7 (2017) 39216–; doi:10.1039/C7RA08157J

data_7228902
_publ_section_title
;
 Asymmetric synthesis of chromene skeletons via organocatalytic domino
 reactions of in situ generated ortho-quinone methide with malononitrile
 and \b-functionalized ketone
;
_journal_issue                   62
_journal_name_full               'RSC Adv.'
_journal_page_first              39216
_journal_paper_doi               10.1039/C7RA08157J
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H27 Br N2 O2'
_chemical_formula_sum            'C24 H27 Br N2 O2'
_chemical_formula_weight         455.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-01-09 deposited with the CCDC.
2017-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.816(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4410(8)
_cell_length_b                   9.3621(7)
_cell_length_c                   11.5467(9)
_cell_measurement_reflns_used    9223
_cell_measurement_temperature    170.03
_cell_measurement_theta_max      68.430
_cell_measurement_theta_min      3.837
_cell_volume                     1126.18(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.03
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27406
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.397
_diffrn_reflns_theta_min         3.837
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.651
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1333 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.5754.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4111
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0997P)^2^+0.5759P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4101
_reflns_number_total             4111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra08157j2.cif
_cod_data_source_block           lipf1
_cod_database_code               7228902
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H19A-H1
 2.2 with sigma of 0.04
3.a Rotating group:
 N1(H1A,H1B)
3.b Ternary CH refined with riding coordinates:
 C3(H3)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C12(H12), C16(H16)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              8450
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'