Chromene-Annulated Bacteriochlorins.
Hyland, Michael A.; Hewage, Nisansala; Panther, Kimberly; Nimthong-Roldán, Arunpatcha; Zeller, Matthias; Samaraweera, Milinda; Gascon, José A; Brückner, Christian; The Journal of organic chemistry 81 (2016) 3603–3618; doi:10.1021/acs.joc.6b00273

data_4036676
_publ_section_title
;
 Chromene-Annulated Bacteriochlorins.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3603
_journal_page_last               3618
_journal_paper_doi               10.1021/acs.joc.6b00273
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C45 H12 F18 N4 O3, 0.4505(C5 H5 N)'
_chemical_formula_sum            'C47.26 H14.26 F18 N4.45 O3'
_chemical_formula_weight         1034.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                85.798(6)
_cell_angle_beta                 72.706(7)
_cell_angle_gamma                78.441(6)
_cell_formula_units_Z            2
_cell_length_a                   10.372(3)
_cell_length_b                   13.120(3)
_cell_length_c                   15.398(4)
_cell_measurement_reflns_used    2929
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.8509
_cell_measurement_theta_min      2.4209
_cell_volume                     1959.9(9)
_computing_cell_refinement       'SAINT V8.18C (Bruker, 2012)'
_computing_data_collection       'Apex2 v2012.4-3 (Bruker, 2012)'
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_computing_structure_refinement
;  
SHELXL-2013 (Sheldrick, 2013), 
SHELXLE Rev609 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.1187
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26746
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.511
_diffrn_reflns_theta_min         2.094
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 v2012.4-3 (Bruker, 2012)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_description       rod
_exptl_crystal_F_000             1029.9
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     747
_refine_ls_number_reflns         11365
_refine_ls_number_restraints     119
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.1767
_refine_ls_R_factor_gt           0.0721
_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^)+(0.0944P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5148
_reflns_number_total             11365
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00273_si_002.cif
_cod_data_source_block           13RNo56_0m
_cod_original_cell_volume        1959.7(9)
_cod_database_code               4036676
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.983
_shelxl_version_number           2012-9
_shelx_res_checksum              20702
_shelx_hkl_checksum              9387